CS164591A3 - Process for preparing beta-hydroxy-alpha aminoacids - Google Patents

Process for preparing beta-hydroxy-alpha aminoacids Download PDF

Info

Publication number: CS164591A3
Authority: CS; Czechoslovakia
Prior art keywords: aldehyde; carbon atoms; formula; alkyl; hydroxy
Prior art date: 1990-06-04

Application number

CS911645A

Other languages

Czech (cs)

English (en)

Inventor

Marvin Joseph Miller

Original Assignee

Univ Notre Dame Du Lac

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1990-06-04

Filing date

1991-05-31

Publication date

1992-01-15

1991-05-31 Application filed by Univ Notre Dame Du Lac filed Critical Univ Notre Dame Du Lac

1992-01-15 Publication of CS164591A3 publication Critical patent/CS164591A3/cs

Links

238000004519 manufacturing process Methods 0.000 title description 2
-1 succinic semialdehyde methyl ester Chemical class 0.000 claims abstract description 92
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims abstract description 64
150000001299 aldehydes Chemical class 0.000 claims abstract description 49
238000000034 method Methods 0.000 claims abstract description 41
239000004471 Glycine Substances 0.000 claims abstract description 32
102000002667 Glycine hydroxymethyltransferase Human genes 0.000 claims abstract description 28
108010043428 Glycine hydroxymethyltransferase Proteins 0.000 claims abstract description 28
125000000217 alkyl group Chemical group 0.000 claims description 25
125000004432 carbon atom Chemical group C* 0.000 claims description 23
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 17
150000001875 compounds Chemical class 0.000 claims description 11
150000003839 salts Chemical class 0.000 claims description 8
125000003342 alkenyl group Chemical group 0.000 claims description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
150000004702 methyl esters Chemical class 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 5
125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000002541 furyl group Chemical group 0.000 claims description 5
125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 claims description 5
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 claims description 4
125000004423 acyloxy group Chemical group 0.000 claims description 4
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims description 4
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
229910019142 PO4 Inorganic materials 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
239000010452 phosphate Substances 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 2
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
150000001340 alkali metals Chemical class 0.000 claims 1
150000001342 alkaline earth metals Chemical class 0.000 claims 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
229910052794 bromium Inorganic materials 0.000 claims 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 1
JNYXCAHRFRIDLS-UHFFFAOYSA-N 5-amino-4-hydroxy-6-methoxy-6-oxohexanoic acid Chemical compound COC(=O)C(N)C(O)CCC(O)=O JNYXCAHRFRIDLS-UHFFFAOYSA-N 0.000 abstract 1
235000008206 alpha-amino acids Nutrition 0.000 abstract 1
230000005494 condensation Effects 0.000 abstract 1
238000009833 condensation Methods 0.000 abstract 1
239000000243 solution Substances 0.000 description 35
102000004190 Enzymes Human genes 0.000 description 33
108090000790 Enzymes Proteins 0.000 description 33
239000000758 substrate Substances 0.000 description 29
238000011534 incubation Methods 0.000 description 26
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
150000001413 amino acids Chemical class 0.000 description 22
239000000047 product Substances 0.000 description 20
239000002253 acid Substances 0.000 description 17
239000000872 buffer Substances 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 15
239000000203 mixture Substances 0.000 description 13
NGVDGCNFYWLIFO-UHFFFAOYSA-N pyridoxal 5'-phosphate Chemical compound CC1=NC=C(COP(O)(O)=O)C(C=O)=C1O NGVDGCNFYWLIFO-UHFFFAOYSA-N 0.000 description 13
235000007682 pyridoxal 5'-phosphate Nutrition 0.000 description 13
239000011589 pyridoxal 5'-phosphate Substances 0.000 description 12
150000002148 esters Chemical class 0.000 description 11
238000004128 high performance liquid chromatography Methods 0.000 description 11
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 9
AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical compound CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 description 8
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 8
230000014759 maintenance of location Effects 0.000 description 8
239000008363 phosphate buffer Substances 0.000 description 8
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
240000008042 Zea mays Species 0.000 description 6
235000002017 Zea mays subsp mays Nutrition 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 5
241000283973 Oryctolagus cuniculus Species 0.000 description 5
125000003118 aryl group Chemical group 0.000 description 5
210000004185 liver Anatomy 0.000 description 5
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 4
MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 4
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 4
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
239000007853 buffer solution Substances 0.000 description 4
235000005822 corn Nutrition 0.000 description 4
230000000694 effects Effects 0.000 description 4
HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 description 4
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 4
102000004169 proteins and genes Human genes 0.000 description 4
108090000623 proteins and genes Proteins 0.000 description 4
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 4
102000007698 Alcohol dehydrogenase Human genes 0.000 description 3
108010021809 Alcohol dehydrogenase Proteins 0.000 description 3
KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
239000004743 Polypropylene Substances 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000003934 aromatic aldehydes Chemical class 0.000 description 3
239000003782 beta lactam antibiotic agent Substances 0.000 description 3
239000012490 blank solution Substances 0.000 description 3
230000002255 enzymatic effect Effects 0.000 description 3
239000012535 impurity Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
238000005949 ozonolysis reaction Methods 0.000 description 3
229920001155 polypropylene Polymers 0.000 description 3
229940120731 pyruvaldehyde Drugs 0.000 description 3
MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 2
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 2
HSJKGGMUJITCBW-UHFFFAOYSA-N 3-hydroxybutanal Chemical compound CC(O)CC=O HSJKGGMUJITCBW-UHFFFAOYSA-N 0.000 description 2
YGCZTXZTJXYWCO-UHFFFAOYSA-N 3-phenylpropanal Chemical compound O=CCCC1=CC=CC=C1 YGCZTXZTJXYWCO-UHFFFAOYSA-N 0.000 description 2
KEHNRUNQZGRQHU-UHFFFAOYSA-N 4-oxopentanal Chemical compound CC(=O)CCC=O KEHNRUNQZGRQHU-UHFFFAOYSA-N 0.000 description 2
241000196324 Embryophyta Species 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
AYFVYJQAPQTCCC-HRFVKAFMSA-N L-allothreonine Chemical compound C[C@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-HRFVKAFMSA-N 0.000 description 2
VHVGNTVUSQUXPS-YUMQZZPRSA-N L-threo-3-phenylserine Chemical class [O-]C(=O)[C@@H]([NH3+])[C@@H](O)C1=CC=CC=C1 VHVGNTVUSQUXPS-YUMQZZPRSA-N 0.000 description 2
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
239000004473 Threonine Substances 0.000 description 2
235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 2
238000005882 aldol condensation reaction Methods 0.000 description 2
125000005907 alkyl ester group Chemical group 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
229910052921 ammonium sulfate Inorganic materials 0.000 description 2
235000011130 ammonium sulphate Nutrition 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
MNFORVFSTILPAW-UHFFFAOYSA-N azetidin-2-one Chemical class O=C1CCN1 MNFORVFSTILPAW-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
JDRMYOQETPMYQX-UHFFFAOYSA-N butanedioic acid monomethyl ester Natural products COC(=O)CCC(O)=O JDRMYOQETPMYQX-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
150000001721 carbon Chemical group 0.000 description 2
125000002843 carboxylic acid group Chemical group 0.000 description 2
MLUCVPSAIODCQM-UHFFFAOYSA-N crotonaldehyde Natural products CC=CC=O MLUCVPSAIODCQM-UHFFFAOYSA-N 0.000 description 2
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239000008367 deionised water Substances 0.000 description 2
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XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004821 distillation Methods 0.000 description 2
238000006911 enzymatic reaction Methods 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 description 2
BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical compound C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 2
239000002243 precursor Substances 0.000 description 2
IJNJLGFTSIAHEA-UHFFFAOYSA-N prop-2-ynal Chemical compound O=CC#C IJNJLGFTSIAHEA-UHFFFAOYSA-N 0.000 description 2
229960001327 pyridoxal phosphate Drugs 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
239000002132 β-lactam antibiotic Substances 0.000 description 2
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IEAUKTACQUVNLS-HNQUOIGGSA-N (e)-3-thiophen-2-ylprop-2-enal Chemical compound O=C\C=C\C1=CC=CS1 IEAUKTACQUVNLS-HNQUOIGGSA-N 0.000 description 1
GKIATJNLLNNGJV-UHFFFAOYSA-N 1-methoxycyclopentene Chemical compound COC1=CCCC1 GKIATJNLLNNGJV-UHFFFAOYSA-N 0.000 description 1
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125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 description 1
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241001465754 Metazoa Species 0.000 description 1
QIKRJDSHBWCYHO-UHFFFAOYSA-N NC(C(C(=O)O)=O)(CC)O Chemical compound NC(C(C(=O)O)=O)(CC)O QIKRJDSHBWCYHO-UHFFFAOYSA-N 0.000 description 1
244000046052 Phaseolus vulgaris Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 1
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 1
IKHGUXGNUITLKF-XPULMUKRSA-N acetaldehyde Chemical compound [14CH]([14CH3])=O IKHGUXGNUITLKF-XPULMUKRSA-N 0.000 description 1
159000000021 acetate salts Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
230000002411 adverse Effects 0.000 description 1
238000005575 aldol reaction Methods 0.000 description 1
150000001323 aldoses Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
239000012431 aqueous reaction media Substances 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
HUMNYLRZRPPJDN-KWCOIAHCSA-N benzaldehyde Chemical group O=[11CH]C1=CC=CC=C1 HUMNYLRZRPPJDN-KWCOIAHCSA-N 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
230000005587 bubbling Effects 0.000 description 1
239000008366 buffered solution Substances 0.000 description 1
QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
235000014633 carbohydrates Nutrition 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
235000013351 cheese Nutrition 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 1
238000013375 chromatographic separation Methods 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
VVYPIVJZLVJPGU-UHFFFAOYSA-L copper;2-aminoacetate Chemical compound [Cu+2].NCC([O-])=O.NCC([O-])=O VVYPIVJZLVJPGU-UHFFFAOYSA-L 0.000 description 1
MLUCVPSAIODCQM-NSCUHMNNSA-N crotonaldehyde Chemical compound C\C=C\C=O MLUCVPSAIODCQM-NSCUHMNNSA-N 0.000 description 1
238000006392 deoxygenation reaction Methods 0.000 description 1
238000010511 deprotection reaction Methods 0.000 description 1
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 description 1
150000005690 diesters Chemical class 0.000 description 1
ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
235000019797 dipotassium phosphate Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
VHJLVAABSRFDPM-QWWZWVQMSA-N dithiothreitol Chemical compound SC[C@@H](O)[C@H](O)CS VHJLVAABSRFDPM-QWWZWVQMSA-N 0.000 description 1
PMNYTGAGAKEGJE-UHFFFAOYSA-N ethane-1,2-diamine;sodium Chemical compound [Na].[Na].NCCN PMNYTGAGAKEGJE-UHFFFAOYSA-N 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
239000004744 fabric Substances 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001917 fluorescence detection Methods 0.000 description 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
239000011521 glass Substances 0.000 description 1
125000001188 haloalkyl group Chemical group 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
125000006038 hexenyl group Chemical group 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000005980 hexynyl group Chemical group 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
125000000904 isoindolyl group Chemical class C=1(NC=C2C=CC=CC12)* 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000004571 lime Substances 0.000 description 1
239000007788 liquid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
PSGAAPLEWMOORI-PEINSRQWSA-N medroxyprogesterone acetate Chemical compound C([C@@]12C)CC(=O)C=C1[C@@H](C)C[C@@H]1[C@@H]2CC[C@]2(C)[C@@](OC(C)=O)(C(C)=O)CC[C@H]21 PSGAAPLEWMOORI-PEINSRQWSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
229940054441 o-phthalaldehyde Drugs 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
125000004043 oxo group Chemical group O=* 0.000 description 1
125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
125000005981 pentynyl group Chemical group 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
ZWLUXSQADUDCSB-UHFFFAOYSA-N phthalaldehyde Chemical compound O=CC1=CC=CC=C1C=O ZWLUXSQADUDCSB-UHFFFAOYSA-N 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000003860 storage Methods 0.000 description 1
150000003900 succinic acid esters Chemical class 0.000 description 1
UIUJIQZEACWQSV-UHFFFAOYSA-N succinic semialdehyde Chemical compound OC(=O)CCC=O UIUJIQZEACWQSV-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
LCZVKKUAUWQDPX-UHFFFAOYSA-N tert-butyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-[2-[(2-methylpropan-2-yl)oxy]-2-oxoethyl]amino]ethyl]amino]acetate Chemical compound CC(=O)OC1=CC=CC=C1CN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC1=CC=CC=C1OC(C)=O LCZVKKUAUWQDPX-UHFFFAOYSA-N 0.000 description 1
150000003588 threonines Chemical class 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N9/00—Enzymes; Proenzymes; Compositions thereof; Processes for preparing, activating, inhibiting, separating or purifying enzymes
- C12N9/10—Transferases (2.)
- C12N9/1003—Transferases (2.) transferring one-carbon groups (2.1)
- C12N9/1014—Hydroxymethyl-, formyl-transferases (2.1.2)
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/24—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having more than one carboxyl group bound to the carbon skeleton, e.g. aspartic acid
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/08—Lysine; Diaminopimelic acid; Threonine; Valine

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Engineering & Computer Science (AREA)
Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Bioinformatics & Cheminformatics (AREA)
Biochemistry (AREA)
General Health & Medical Sciences (AREA)
Microbiology (AREA)
Biotechnology (AREA)
General Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Molecular Biology (AREA)
Medicinal Chemistry (AREA)
Biomedical Technology (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Catalysts (AREA)
Diaphragms For Electromechanical Transducers (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)

CS911645A 1990-06-04 1991-05-31 Process for preparing beta-hydroxy-alpha aminoacids CS164591A3 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US53284590A	1990-06-04	1990-06-04

Publications (1)

Publication Number	Publication Date
CS164591A3 true CS164591A3 (en)	1992-01-15

Family

ID=24123416

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS911645A CS164591A3 (en)	1990-06-04	1991-05-31	Process for preparing beta-hydroxy-alpha aminoacids

Country Status (20)

Country	Link
EP (1)	EP0460883B1 (de)
JP (1)	JPH0787989A (de)
KR (1)	KR920000701A (de)
CN (1)	CN1058046A (de)
AT (1)	ATE147785T1 (de)
AU (1)	AU637705B2 (de)
CA (1)	CA2043761A1 (de)
CS (1)	CS164591A3 (de)
DE (1)	DE69124143T2 (de)
DK (1)	DK0460883T3 (de)
ES (1)	ES2099135T3 (de)
FI (1)	FI912626A7 (de)
GR (1)	GR3022558T3 (de)
HU (1)	HU212925B (de)
IE (1)	IE911879A1 (de)
IL (1)	IL98312A0 (de)
NO (1)	NO912120L (de)
NZ (1)	NZ238342A (de)
YU (1)	YU97891A (de)
ZA (1)	ZA914201B (de)

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* Cited by examiner, † Cited by third party
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EP0628638A3 (de) *	1993-05-25	1995-09-06	Lilly Co Eli	Verfahren zur Herstellung von 2-Amino-3-Hydroxy-Karbonsäuren.
JP4032441B2 (ja) *	1995-08-30	2008-01-16	味の素株式会社	Ｌ−アミノ酸の製造方法
CN1062603C (zh) *	1996-01-31	2001-02-28	中国科学院大连化学物理研究所	酶法生产d－对羟基苯甘氨酸的膜反应方法
CA2234412C (en) *	1997-06-09	2008-09-02	Kyowa Hakko Kogyo Co., Ltd.	Method for producing optically active compound
WO2003090918A1 (en)	2002-04-26	2003-11-06	China Petroleum & Chemical Corporation	Downflow catalytic cracking reactor and use thereof
DE102007020246B4 (de)	2007-04-24	2012-12-27	Schott Ag	Metallkolloidgefärbte oder farblose Glaskeramik und in eine metallkolloidgefärbte oder farblose Glaskeramik umwandelbares farbloses Glas
US20160326157A1 (en) *	2014-01-06	2016-11-10	President And Fellows Of Harvard College	Monobactams and methods of their synthesis and use
EP3630798B1 (de) *	2017-05-27	2022-11-23	Enzymaster (Ningbo) Bio-Engineering Co., Ltd.	Veränderte aldolase polypeptide und deren anwendung in der synthese von beta-hydroxy-alpha-aminosäuren
CN114657221A (zh) *	2020-12-22	2022-06-24	安徽华恒生物科技股份有限公司	一种d-泛酸的制备方法

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3871958A (en) *	1972-03-04	1975-03-18	Ajinomoto Kk	Biological method of producing serine and serinol derivatives
JPS59109187A (ja) *	1982-11-19	1984-06-23	ジェネックス・コーポレイション	Ｌ−セリンの酵素的合成方法

1991
- 1991-05-30 NZ NZ238342A patent/NZ238342A/en unknown
- 1991-05-30 IL IL98312A patent/IL98312A0/xx unknown
- 1991-05-31 IE IE187991A patent/IE911879A1/en unknown
- 1991-05-31 KR KR1019910008978A patent/KR920000701A/ko not_active Ceased
- 1991-05-31 FI FI912626A patent/FI912626A7/fi not_active Application Discontinuation
- 1991-05-31 CS CS911645A patent/CS164591A3/cs unknown
- 1991-06-03 JP JP3131068A patent/JPH0787989A/ja active Pending
- 1991-06-03 YU YU97891A patent/YU97891A/sh unknown
- 1991-06-03 CA CA002043761A patent/CA2043761A1/en not_active Abandoned
- 1991-06-03 EP EP91304977A patent/EP0460883B1/de not_active Expired - Lifetime
- 1991-06-03 ES ES91304977T patent/ES2099135T3/es not_active Expired - Lifetime
- 1991-06-03 DE DE69124143T patent/DE69124143T2/de not_active Expired - Fee Related
- 1991-06-03 CN CN91104369A patent/CN1058046A/zh active Pending
- 1991-06-03 AU AU78146/91A patent/AU637705B2/en not_active Ceased
- 1991-06-03 AT AT91304977T patent/ATE147785T1/de active
- 1991-06-03 ZA ZA914201A patent/ZA914201B/xx unknown
- 1991-06-03 HU HU911854A patent/HU212925B/hu not_active IP Right Cessation
- 1991-06-03 DK DK91304977.1T patent/DK0460883T3/da active
- 1991-06-03 NO NO91912120A patent/NO912120L/no unknown
1997
- 1997-02-12 GR GR970400248T patent/GR3022558T3/el unknown

Also Published As

Publication number	Publication date
DK0460883T3 (da)	1997-07-14
CA2043761A1 (en)	1991-12-05
EP0460883A2 (de)	1991-12-11
ES2099135T3 (es)	1997-05-16
KR920000701A (ko)	1992-01-29
GR3022558T3 (en)	1997-05-31
ZA914201B (en)	1993-02-24
FI912626L (fi)	1991-12-05
IL98312A0 (en)	1992-06-21
FI912626A7 (fi)	1991-12-05
AU7814691A (en)	1991-12-05
FI912626A0 (fi)	1991-05-31
ATE147785T1 (de)	1997-02-15
DE69124143T2 (de)	1997-05-22
EP0460883A3 (en)	1992-11-19
NO912120D0 (no)	1991-06-03
IE911879A1 (en)	1991-12-04
DE69124143D1 (de)	1997-02-27
EP0460883B1 (de)	1997-01-15
CN1058046A (zh)	1992-01-22
YU97891A (sh)	1994-01-20
HU212925B (en)	1996-12-30
HUT61597A (en)	1993-01-28
HU911854D0 (en)	1991-12-30
NZ238342A (en)	1993-10-26
JPH0787989A (ja)	1995-04-04
AU637705B2 (en)	1993-06-03
NO912120L (no)	1991-12-05

Publication	Publication Date	Title
CA2637821A1 (en)	2007-08-23	Process for the preparation of optically active chiral amines
Rando	1977	Mechanism of the irreversible inhibition of γ-aminobutyric acid-α-ketoglutaric acid transaminase by the neurotoxin gabaculine
OZAKI et al.	1969	Regulation of the TCA and glyoxylate cycles in Brevibacterium flavum: II. Regulation of phosphoenolpyruvate carboxylase and pyruvate kinase
Soda et al.	1968	L-lysine-. alpha.-ketoglutarate aminotransferase. I. Identification of a product,. DELTA. 1-piperideine-6-carboxylic acid
Silverman et al.	1981	Mechanism of inactivation of. gamma.-aminobutyric acid-. alpha.-ketoglutaric acid aminotransferase by 4-amino-5-halopentanoic acids
CS164591A3 (en)	1992-01-15	Process for preparing beta-hydroxy-alpha aminoacids
Laber et al.	1994	Mechanisms of interaction of Escherichia coli threonine synthase with substrates and inhibitors
US3871958A (en)	1975-03-18	Biological method of producing serine and serinol derivatives
KR100810169B1 (ko)	2008-03-06	아스파르테이트를 사용하여 효소적 아미노기 전달반응에의해 엘-포스피노트리신을 제조하는 방법
Bearne et al.	1995	Glutamate. gamma.-semialdehyde as a natural transition state analog inhibitor of Escherichia coli glucosamine-6-phosphate synthase
Chase et al.	1966	A coenzyme A analogue, desulpho-coA; preparation and effects on various enzymes
NO166083B (no)	1991-02-18	Analogifremgangsmaate ved fremstilling av terapeutisk aktive pyridazodiazepinderivater.
EP1897956A1 (de)	2008-03-12	Verfahren zur Herstellung von optisch aktiven Aminen durch Racematspaltung unter Verwendung einer bakteriellen omega-Transaminase
EP0175312B1 (de)	1991-01-09	Verfahren zur Herstellung von optisch aktiven Hydantoinen
CS224638B2 (en)	1984-01-16	Method of enzymetic cleavage d,l-2-amino-4-methylphosphinebutyric acid
US5266468A (en)	1993-11-30	Process for preparing β-hydroxy-α amino acids
CZ20003223A3 (cs)	2000-11-15	Způsob enzymatického dělení enantiomerů 3(R)- a 3(S)-hydroxy-1-methyl-4(2,4,6-trimethoxyfenyl)-1,2,3,6-tetrahydropyridinu, popřípadě esterů karboxylových kyselin
Bailey et al.	1995	Synthesis of 4a-hydroxytetrahydropterins and the mechanism of their nonenzymic dehydration to quinoid dihydropterins
Gamini Kannangara et al.	1978	Biosynthesis of Δ-aminolevulinate in greening barley leaves: Glutamate 1-semialdehyde aminotransferase
Guibé-Jampel et al.	1987	Enantioselective hydrolysis of racemic diesters by porcine pancreatic lipase
TRINCHANT et al.	1974	Lactate dehydrogenase from Rhizobium. Purification and role in indole metabolism
Westerik et al.	1974	Aspartic-β-Semialdehyde: A Potent Inhibitor of Escherichia coli l-Asparaginase
Fulston et al.	2001	Clavulanic acid biosynthesis; the final steps
NAM et al.	1984	Enzymatic synthesis of phenoxymethylpenicillin using Erwinia aroideae enzyme
NZ225806A (en)	1991-04-26	Process for the resolution of dialkylphosphinoyl hydroxy acetic acid esters, the acid so obtained, and plant growth control compositions containing it