CH679672A5 - - Google Patents

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Publication number: CH679672A5
Authority: CH; Switzerland
Prior art keywords: meth; acryloyl; washing; dmf; coupling
Prior art date: 1988-09-24

Application number

CH3435/89A

Other languages

English (en)

French (fr)

Inventor

Bernard Calas

Michel Follet

Jean Mery

Hanitra Naharisoa

Original Assignee

Expansion Scientifiqueexpansia

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.)

1988-09-24

Filing date

1989-09-21

Publication date

1992-03-31

1989-09-21 Application filed by Expansion Scientifiqueexpansia filed Critical Expansion Scientifiqueexpansia

1992-03-31 Publication of CH679672A5 publication Critical patent/CH679672A5/fr

Links

XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 40
239000011347 resin Substances 0.000 claims description 31
229920005989 resin Polymers 0.000 claims description 31
239000000243 solution Substances 0.000 claims description 27
238000005406 washing Methods 0.000 claims description 23
108090000765 processed proteins & peptides Proteins 0.000 claims description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 18
238000000034 method Methods 0.000 claims description 18
230000008878 coupling Effects 0.000 claims description 16
238000010168 coupling process Methods 0.000 claims description 16
238000005859 coupling reaction Methods 0.000 claims description 16
239000012153 distilled water Substances 0.000 claims description 14
229940024606 amino acid Drugs 0.000 claims description 11
150000001413 amino acids Chemical class 0.000 claims description 11
150000008064 anhydrides Chemical class 0.000 claims description 11
229920001577 copolymer Polymers 0.000 claims description 10
239000000178 monomer Substances 0.000 claims description 9
238000010511 deprotection reaction Methods 0.000 claims description 7
238000006386 neutralization reaction Methods 0.000 claims description 7
239000004925 Acrylic resin Substances 0.000 claims description 6
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 6
238000010647 peptide synthesis reaction Methods 0.000 claims description 6
239000007790 solid phase Substances 0.000 claims description 6
239000002253 acid Substances 0.000 claims description 5
125000000539 amino acid group Chemical group 0.000 claims description 5
HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 claims description 4
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 claims description 4
150000007513 acids Chemical class 0.000 claims description 4
239000011159 matrix material Substances 0.000 claims description 4
229960004441 tyrosine Drugs 0.000 claims description 4
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 claims description 3
BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 claims description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
UTDSSTFBUGDVAI-LURJTMIESA-N (2s)-1-prop-2-enoylpyrrolidine-2-carboxylic acid Chemical compound OC(=O)[C@@H]1CCCN1C(=O)C=C UTDSSTFBUGDVAI-LURJTMIESA-N 0.000 claims description 2
PPRBGMXQDAMDAB-BYPYZUCNSA-N (2s)-2-(prop-2-enoylamino)propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)C=C PPRBGMXQDAMDAB-BYPYZUCNSA-N 0.000 claims description 2
UHWCAAMSQLMQKV-ZETCQYMHSA-N (2s)-3-methyl-2-(prop-2-enoylamino)butanoic acid Chemical compound CC(C)[C@@H](C(O)=O)NC(=O)C=C UHWCAAMSQLMQKV-ZETCQYMHSA-N 0.000 claims description 2
SAQWCPXBLNGTCC-UHFFFAOYSA-N 6-(prop-2-enoylamino)hexanoic acid Chemical compound OC(=O)CCCCCNC(=O)C=C SAQWCPXBLNGTCC-UHFFFAOYSA-N 0.000 claims description 2
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims description 2
239000004395 L-leucine Substances 0.000 claims description 2
101100074998 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) nmp-2 gene Proteins 0.000 claims description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 2
230000003213 activating effect Effects 0.000 claims description 2
239000007864 aqueous solution Substances 0.000 claims description 2
239000003431 cross linking reagent Substances 0.000 claims description 2
229960003136 leucine Drugs 0.000 claims description 2
229960004452 methionine Drugs 0.000 claims description 2
150000004702 methyl esters Chemical class 0.000 claims description 2
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 2
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 32
YMWUJEATGCHHMB-UHFFFAOYSA-N dichloromethane Natural products ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 25
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 11
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
239000000203 mixture Substances 0.000 description 9
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 8
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 6
238000001914 filtration Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
238000011282 treatment Methods 0.000 description 5
-1 Boc group Chemical group 0.000 description 4
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000002904 solvent Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
VWWKKDNCCLAGRM-GVXVVHGQSA-N (2s)-2-[[2-[[(2s)-2-[[(2s)-2-amino-4-methylpentanoyl]amino]propanoyl]amino]acetyl]amino]-3-methylbutanoic acid Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)NCC(=O)N[C@@H](C(C)C)C(O)=O VWWKKDNCCLAGRM-GVXVVHGQSA-N 0.000 description 3
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
AHVYPIQETPWLSZ-UHFFFAOYSA-N N-methyl-pyrrolidine Natural products CN1CC=CC1 AHVYPIQETPWLSZ-UHFFFAOYSA-N 0.000 description 3
SECXISVLQFMRJM-UHFFFAOYSA-N NMP Substances CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
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102000004196 processed proteins & peptides Human genes 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
102000004169 proteins and genes Human genes 0.000 description 3
FUKOTTQGWQVMQB-UHFFFAOYSA-N (2-bromoacetyl) 2-bromoacetate Chemical compound BrCC(=O)OC(=O)CBr FUKOTTQGWQVMQB-UHFFFAOYSA-N 0.000 description 2
ZQEBQGAAWMOMAI-ZETCQYMHSA-N (2s)-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid Chemical compound CC(C)(C)OC(=O)N1CCC[C@H]1C(O)=O ZQEBQGAAWMOMAI-ZETCQYMHSA-N 0.000 description 2
CNBUSIJNWNXLQQ-NSHDSACASA-N (2s)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 CNBUSIJNWNXLQQ-NSHDSACASA-N 0.000 description 2
TZGPACAKMCUCKX-UHFFFAOYSA-N 2-hydroxyacetamide Chemical compound NC(=O)CO TZGPACAKMCUCKX-UHFFFAOYSA-N 0.000 description 2
RJPKQCFHEPPTGL-ZLUOBGJFSA-N Cys-Ser-Asp Chemical compound [H]N[C@@H](CS)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC(O)=O)C(O)=O RJPKQCFHEPPTGL-ZLUOBGJFSA-N 0.000 description 2
QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 description 2
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QNAYBMKLOCPYGJ-UWTATZPHSA-N L-Alanine Natural products C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 description 2
IBMVEYRWAWIOTN-UHFFFAOYSA-N L-Leucyl-L-Arginyl-L-Proline Natural products CC(C)CC(N)C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(O)=O IBMVEYRWAWIOTN-UHFFFAOYSA-N 0.000 description 2
JKGHDYGZRDWHGA-SRVKXCTJSA-N Leu-Asn-Leu Chemical compound [H]N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(O)=O JKGHDYGZRDWHGA-SRVKXCTJSA-N 0.000 description 2
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CGOMLCQJEMWMCE-STQMWFEESA-N Phe-Arg-Gly Chemical compound NC(N)=NCCC[C@@H](C(=O)NCC(O)=O)NC(=O)[C@@H](N)CC1=CC=CC=C1 CGOMLCQJEMWMCE-STQMWFEESA-N 0.000 description 2
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QKQDTEYDEIJPNK-GUBZILKMSA-N Ser-Glu-Lys Chemical compound NCCCC[C@@H](C(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](N)CO QKQDTEYDEIJPNK-GUBZILKMSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
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GGXUDPQWAWRINY-XEGUGMAKSA-N Tyr-Ile-Gly Chemical compound OC(=O)CNC(=O)[C@H]([C@@H](C)CC)NC(=O)[C@@H](N)CC1=CC=C(O)C=C1 GGXUDPQWAWRINY-XEGUGMAKSA-N 0.000 description 2
JAGGEZACYAAMIL-CQDKDKBSSA-N Tyr-Lys-Ala Chemical compound C[C@@H](C(=O)O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC1=CC=C(C=C1)O)N JAGGEZACYAAMIL-CQDKDKBSSA-N 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 2
210000005253 yeast cell Anatomy 0.000 description 2
DMBKPDOAQVGTST-LBPRGKRZSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylmethoxypropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)COCC1=CC=CC=C1 DMBKPDOAQVGTST-LBPRGKRZSA-N 0.000 description 1
ADFXKUOMJKEIND-UHFFFAOYSA-N 1,3-dicyclohexylurea Chemical compound C1CCCCC1NC(=O)NC1CCCCC1 ADFXKUOMJKEIND-UHFFFAOYSA-N 0.000 description 1
AVFZOVWCLRSYKC-UHFFFAOYSA-N 1-methylpyrrolidine Chemical compound CN1CCCC1 AVFZOVWCLRSYKC-UHFFFAOYSA-N 0.000 description 1
125000003287 1H-imidazol-4-ylmethyl group Chemical group [H]N1C([H])=NC(C([H])([H])[*])=C1[H] 0.000 description 1
WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 1
241000024188 Andala Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
125000000030 D-alanine group Chemical group [H]N([H])[C@](C([H])([H])[H])(C(=O)[*])[H] 0.000 description 1
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QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
WNGVUZWBXZKQES-YUMQZZPRSA-N Leu-Ala-Gly Chemical compound CC(C)C[C@H](N)C(=O)N[C@@H](C)C(=O)NCC(O)=O WNGVUZWBXZKQES-YUMQZZPRSA-N 0.000 description 1
MDXGYYOJGPFFJL-QMMMGPOBSA-N N(alpha)-t-butoxycarbonyl-L-leucine Chemical compound CC(C)C[C@@H](C(O)=O)NC(=O)OC(C)(C)C MDXGYYOJGPFFJL-QMMMGPOBSA-N 0.000 description 1
NFVNYBJCJGKVQK-ZDUSSCGKSA-N N-[(Tert-butoxy)carbonyl]-L-tryptophan Chemical compound C1=CC=C2C(C[C@H](NC(=O)OC(C)(C)C)C(O)=O)=CNC2=C1 NFVNYBJCJGKVQK-ZDUSSCGKSA-N 0.000 description 1
102000001253 Protein Kinase Human genes 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
229960003767 alanine Drugs 0.000 description 1
KPGVUOQMOHGHEW-LBPRGKRZSA-N boc-his(dnp)-oh Chemical compound C1=NC(C[C@H](NC(=O)OC(C)(C)C)C(O)=O)=CN1C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O KPGVUOQMOHGHEW-LBPRGKRZSA-N 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
238000003776 cleavage reaction Methods 0.000 description 1
238000007334 copolymerization reaction Methods 0.000 description 1
DEZRYPDIMOWBDS-UHFFFAOYSA-N dcm dichloromethane Chemical compound ClCCl.ClCCl DEZRYPDIMOWBDS-UHFFFAOYSA-N 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
125000006286 dichlorobenzyl group Chemical group 0.000 description 1
UXGNZZKBCMGWAZ-UHFFFAOYSA-N dimethylformamide dmf Chemical compound CN(C)C=O.CN(C)C=O UXGNZZKBCMGWAZ-UHFFFAOYSA-N 0.000 description 1
ZFKJVJIDPQDDFY-UHFFFAOYSA-N fluorescamine Chemical compound C12=CC=CC=C2C(=O)OC1(C1=O)OC=C1C1=CC=CC=C1 ZFKJVJIDPQDDFY-UHFFFAOYSA-N 0.000 description 1
XLXSAKCOAKORKW-UHFFFAOYSA-N gonadorelin Chemical class C1CCC(C(=O)NCC(N)=O)N1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)CNC(=O)C(NC(=O)C(CO)NC(=O)C(CC=1C2=CC=CC=C2NC=1)NC(=O)C(CC=1NC=NC=1)NC(=O)C1NC(=O)CC1)CC1=CC=C(O)C=C1 XLXSAKCOAKORKW-UHFFFAOYSA-N 0.000 description 1
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 1
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
229940100630 metacresol Drugs 0.000 description 1
VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 1
AYGYHGXUJBFUJU-UHFFFAOYSA-N n-[2-(prop-2-enoylamino)ethyl]prop-2-enamide Chemical compound C=CC(=O)NCCNC(=O)C=C AYGYHGXUJBFUJU-UHFFFAOYSA-N 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
XTUSEBKMEQERQV-UHFFFAOYSA-N propan-2-ol;hydrate Chemical compound O.CC(C)O XTUSEBKMEQERQV-UHFFFAOYSA-N 0.000 description 1
108060006633 protein kinase Proteins 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/04—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length on carriers

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Analytical Chemistry (AREA)
Peptides Or Proteins (AREA)
Polymerization Catalysts (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CH3435/89A 1988-09-24 1989-09-21 CH679672A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB888822502A GB8822502D0 (en)	1988-09-24	1988-09-24	New peptide synthesis method

Publications (1)

Publication Number	Publication Date
CH679672A5 true CH679672A5 (de)	1992-03-31

Family

ID=10644204

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH3435/89A CH679672A5 (de)	1988-09-24	1989-09-21

Country Status (30)

Country	Link
JP (1)	JPH0768265B2 (de)
KR (1)	KR900004761A (de)
AR (1)	AR244701A1 (de)
AT (1)	AT400439B (de)
AU (1)	AU622705B2 (de)
BE (1)	BE1002237A3 (de)
CA (1)	CA1333441C (de)
CH (1)	CH679672A5 (de)
DE (1)	DE3931731C2 (de)
DK (1)	DK468589A (de)
ES (1)	ES2018924A6 (de)
FI (1)	FI101474B1 (de)
FR (1)	FR2636951B1 (de)
GB (2)	GB8822502D0 (de)
GR (1)	GR1000564B (de)
HK (1)	HK47792A (de)
IE (1)	IE62008B1 (de)
IT (1)	IT1231960B (de)
LU (1)	LU87592A1 (de)
MA (1)	MA21633A1 (de)
MY (1)	MY106567A (de)
NL (1)	NL8902361A (de)
NO (1)	NO175593C (de)
NZ (1)	NZ230712A (de)
OA (1)	OA09243A (de)
PT (1)	PT91784B (de)
SE (1)	SE8903121L (de)
SG (1)	SG40692G (de)
TN (1)	TNSN89104A1 (de)
ZA (1)	ZA897151B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5811241A (en) *	1995-09-13	1998-09-22	Cortech, Inc.	Method for preparing and identifying N-substitued 1,4-piperazines and N-substituted 1,4-piperazinediones
DE60123115T2 (de) *	2000-12-22	2007-03-29	Ipsen Manufacturing Ireland Ltd.	Verfahren für die synthese eines lhrh peptides

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3951741A (en) *	1973-07-10	1976-04-20	Peter Pfaender	Process and apparatus for the synthesis of peptides by use of n-carboxyanhydrides
US4436874A (en) *	1981-11-19	1984-03-13	Societe D'expansion Scientifique "Expansia"	Acrylic copolymers and their use in solid phase peptide synthesis

1988
- 1988-09-24 GB GB888822502A patent/GB8822502D0/en active Pending
1989
- 1989-09-18 GR GR890100587A patent/GR1000564B/el unknown
- 1989-09-19 ZA ZA897151A patent/ZA897151B/xx unknown
- 1989-09-19 BE BE8901003A patent/BE1002237A3/fr not_active IP Right Cessation
- 1989-09-20 NZ NZ230712A patent/NZ230712A/en unknown
- 1989-09-20 AR AR89314966A patent/AR244701A1/es active
- 1989-09-20 AT AT0219989A patent/AT400439B/de not_active IP Right Cessation
- 1989-09-21 NL NL8902361A patent/NL8902361A/nl active Search and Examination
- 1989-09-21 FR FR898912394A patent/FR2636951B1/fr not_active Expired - Fee Related
- 1989-09-21 ES ES8903198A patent/ES2018924A6/es not_active Expired - Lifetime
- 1989-09-21 MY MYPI89001300A patent/MY106567A/en unknown
- 1989-09-21 CH CH3435/89A patent/CH679672A5/fr not_active IP Right Cessation
- 1989-09-21 LU LU87592A patent/LU87592A1/fr unknown
- 1989-09-22 IT IT8921804A patent/IT1231960B/it active
- 1989-09-22 DK DK468589A patent/DK468589A/da not_active Application Discontinuation
- 1989-09-22 SE SE8903121A patent/SE8903121L/ not_active Application Discontinuation
- 1989-09-22 OA OA59652A patent/OA09243A/xx unknown
- 1989-09-22 FI FI894489A patent/FI101474B1/fi not_active IP Right Cessation
- 1989-09-22 JP JP1245374A patent/JPH0768265B2/ja not_active Expired - Lifetime
- 1989-09-22 AU AU41614/89A patent/AU622705B2/en not_active Ceased
- 1989-09-22 PT PT91784A patent/PT91784B/pt active IP Right Revival
- 1989-09-22 CA CA000612438A patent/CA1333441C/en not_active Expired - Fee Related
- 1989-09-22 TN TNTNSN89104A patent/TNSN89104A1/fr unknown
- 1989-09-22 MA MA21887A patent/MA21633A1/fr unknown
- 1989-09-22 NO NO893773A patent/NO175593C/no not_active IP Right Cessation
- 1989-09-22 DE DE3931731A patent/DE3931731C2/de not_active Expired - Fee Related
- 1989-09-22 IE IE303789A patent/IE62008B1/en not_active IP Right Cessation
- 1989-09-23 KR KR1019890013716A patent/KR900004761A/ko not_active Ceased
- 1989-09-25 GB GB8921637A patent/GB2223227B/en not_active Expired - Fee Related
1992
- 1992-04-14 SG SG406/92A patent/SG40692G/en unknown
- 1992-07-02 HK HK477/92A patent/HK47792A/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
BE1002237A3 (fr)	1990-10-30
GB2223227B (en)	1992-01-15
TNSN89104A1 (fr)	1991-02-04
ES2018924A6 (es)	1991-05-16
IE62008B1 (en)	1994-12-14
NO175593B (no)	1994-07-25
GR1000564B (el)	1992-08-26
MY106567A (en)	1995-06-30
CA1333441C (en)	1994-12-06
FI894489L (fi)	1990-03-25
FI894489A0 (fi)	1989-09-22
HK47792A (en)	1992-07-10
AU4161489A (en)	1990-03-29
PT91784B (pt)	1996-01-31
FR2636951A1 (fr)	1990-03-30
OA09243A (en)	1992-06-30
KR900004761A (ko)	1990-04-13
NZ230712A (en)	1991-07-26
NO893773L (no)	1990-03-26
LU87592A1 (fr)	1990-01-08
SG40692G (en)	1992-06-12
MA21633A1 (fr)	1990-04-01
ZA897151B (en)	1990-06-27
IE893037L (en)	1990-03-24
FI101474B (fi)	1998-06-30
JPH0768265B2 (ja)	1995-07-26
IT1231960B (it)	1992-01-16
FI101474B1 (fi)	1998-06-30
GR890100587A (en)	1990-10-31
GB8921637D0 (en)	1989-11-08
AR244701A1 (es)	1993-11-30
NO893773D0 (no)	1989-09-22
GB2223227A (en)	1990-04-04
DK468589A (da)	1990-03-25
FR2636951B1 (fr)	1991-03-08
AT400439B (de)	1995-12-27
DE3931731C2 (de)	1996-06-13
GB8822502D0 (en)	1988-10-26
NL8902361A (nl)	1990-04-17
ATA219989A (de)	1995-05-15
AU622705B2 (en)	1992-04-16
PT91784A (pt)	1990-03-30
SE8903121L (sv)	1990-03-25
JPH02129200A (ja)	1990-05-17
NO175593C (no)	1994-11-02
SE8903121D0 (sv)	1989-09-22
IT8921804A0 (it)	1989-09-22
DE3931731A1 (de)	1990-03-29
DK468589D0 (da)	1989-09-22

Legal Events

Date	Code	Title	Description
2001-05-15	PL	Patent ceased

Publication	Publication Date	Title
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EP0081408B1 (de)	1987-07-22	Äthylendiamin funktionelle Acrylharze und Verfahren zur Herstellung
JPS6140680B2 (de)	1986-09-10
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US6897289B1 (en)	2005-05-24	Peptide synthesis procedure in solid phase
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FR2803594A1 (fr)	2001-07-13	Oligomeres de mimes contraints non peptidiques de dipeptides ou de tripeptides, et leurs utilisations
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AU2002316989B2 (en)	2006-10-26	Glycopeptides, their preparation and use in the diagnosis or therapeutic treatment of multiple sclerosis
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US7176282B1 (en)	2007-02-13	Solid-phase peptide synthesis and agent for use in such synthesis
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AU597827B2 (en)	1990-06-07	Allylic side chain-containing solid phase systems, processes for the preparation thereof and the use thereof in solid phase reactions
JPH0676436B2 (ja)	1994-09-28	新規な生理活性ペプチド
Remmer et al.	2000	Chemical synthesis of peptides