DD298932A5 - Verfahren zur herstellung von peptidalkoholen - Google Patents

Verfahren zur herstellung von peptidalkoholen Download PDF

Info

Publication number: DD298932A5
Authority: DD; German Democratic Republic
Prior art keywords: group; alcohol; resin; formula; radical
Prior art date: 1987-08-17

Application number

DD88318954A

Other languages

German (de)

English (en)

Inventor

Monika Mergler

Walter Priskoszovich

Original Assignee

��`��`��k��

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.)

1987-08-17

Filing date

1988-08-15

Publication date

1992-03-19

1988-08-15 Application filed by ��`��`��k�� filed Critical ��`��`��k��

1992-03-19 Publication of DD298932A5 publication Critical patent/DD298932A5/de

Links

108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 33
150000001298 alcohols Chemical class 0.000 title claims abstract description 8
238000004519 manufacturing process Methods 0.000 title description 3
229920005989 resin Polymers 0.000 claims abstract description 32
239000011347 resin Substances 0.000 claims abstract description 32
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 20
238000000034 method Methods 0.000 claims abstract description 20
239000007790 solid phase Substances 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 11
125000003158 alcohol group Chemical group 0.000 claims abstract description 8
210000004899 c-terminal region Anatomy 0.000 claims abstract description 7
125000003396 thiol group Chemical group [H]S* 0.000 claims abstract 4
150000001875 compounds Chemical class 0.000 claims description 12
229920000642 polymer Polymers 0.000 claims description 10
125000006239 protecting group Chemical group 0.000 claims description 10
239000004793 Polystyrene Substances 0.000 claims description 6
229920002223 polystyrene Polymers 0.000 claims description 6
125000004036 acetal group Chemical group 0.000 claims description 5
230000002378 acidificating effect Effects 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
238000003776 cleavage reaction Methods 0.000 description 11
230000007017 scission Effects 0.000 description 11
235000001014 amino acid Nutrition 0.000 description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
150000001413 amino acids Chemical class 0.000 description 8
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 7
-1 polyethylene Polymers 0.000 description 7
229920001184 polypeptide Polymers 0.000 description 7
102000004196 processed proteins & peptides Human genes 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
125000006850 spacer group Chemical group 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
125000003277 amino group Chemical group 0.000 description 4
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
235000019256 formaldehyde Nutrition 0.000 description 4
229960004279 formaldehyde Drugs 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
150000001414 amino alcohols Chemical class 0.000 description 3
230000015572 biosynthetic process Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
230000007062 hydrolysis Effects 0.000 description 3
238000006460 hydrolysis reaction Methods 0.000 description 3
230000003647 oxidation Effects 0.000 description 3
238000007254 oxidation reaction Methods 0.000 description 3
MUVQIIBPDFTEKM-QWWZWVQMSA-N (2r,3r)-2-aminobutane-1,3-diol Chemical compound C[C@@H](O)[C@H](N)CO MUVQIIBPDFTEKM-QWWZWVQMSA-N 0.000 description 2
JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 2
SLXKOJJOQWFEFD-UHFFFAOYSA-N 6-aminohexanoic acid Chemical compound NCCCCCC(O)=O SLXKOJJOQWFEFD-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
229960002684 aminocaproic acid Drugs 0.000 description 2
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
238000010276 construction Methods 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000001914 filtration Methods 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 2
JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
229920005990 polystyrene resin Polymers 0.000 description 2
239000002243 precursor Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
238000005406 washing Methods 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
ZWAJLVLEBYIOTI-OLQVQODUSA-N (1s,6r)-7-oxabicyclo[4.1.0]heptane Chemical compound C1CCC[C@@H]2O[C@@H]21 ZWAJLVLEBYIOTI-OLQVQODUSA-N 0.000 description 1
125000003088 (fluoren-9-ylmethoxy)carbonyl group Chemical group 0.000 description 1
ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
KJJPLEZQSCZCKE-UHFFFAOYSA-N 2-aminopropane-1,3-diol Chemical compound OCC(N)CO KJJPLEZQSCZCKE-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
239000005695 Ammonium acetate Substances 0.000 description 1
101800001415 Bri23 peptide Proteins 0.000 description 1
125000001433 C-terminal amino-acid group Chemical group 0.000 description 1
102400000107 C-terminal peptide Human genes 0.000 description 1
101800000655 C-terminal peptide Proteins 0.000 description 1
QIVBCDIJIAJPQS-SECBINFHSA-N D-tryptophane Chemical compound C1=CC=C2C(C[C@@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-SECBINFHSA-N 0.000 description 1
241001416537 Gliridae Species 0.000 description 1
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
RHQDFWAXVIIEBN-UHFFFAOYSA-N Trifluoroethanol Chemical compound OCC(F)(F)F RHQDFWAXVIIEBN-UHFFFAOYSA-N 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
230000009435 amidation Effects 0.000 description 1
238000007112 amidation reaction Methods 0.000 description 1
235000019257 ammonium acetate Nutrition 0.000 description 1
229940043376 ammonium acetate Drugs 0.000 description 1
239000012062 aqueous buffer Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
125000005521 carbonamide group Chemical group 0.000 description 1
PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
241001233037 catfish Species 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000012045 crude solution Substances 0.000 description 1
XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
235000018417 cysteine Nutrition 0.000 description 1
125000000151 cysteine group Chemical group N[C@@H](CS)C(=O)* 0.000 description 1
238000010828 elution Methods 0.000 description 1
230000032050 esterification Effects 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
238000004128 high performance liquid chromatography Methods 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
238000010348 incorporation Methods 0.000 description 1
125000000468 ketone group Chemical group 0.000 description 1
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
238000010647 peptide synthesis reaction Methods 0.000 description 1
229920002401 polyacrylamide Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
238000010926 purge Methods 0.000 description 1
238000006894 reductive elimination reaction Methods 0.000 description 1
239000012262 resinous product Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
125000004149 thio group Chemical group *S* 0.000 description 1
HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
239000005051 trimethylchlorosilane Substances 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
- C07K1/107—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides
- C07K1/1072—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups
- C07K1/1077—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length by chemical modification of precursor peptides by covalent attachment of residues or functional groups by covalent attachment of residues other than amino acids or peptide residues, e.g. sugars, polyols, fatty acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Biophysics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Medicinal Chemistry (AREA)
Analytical Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Peptides Or Proteins (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

DD88318954A 1987-08-17 1988-08-15 Verfahren zur herstellung von peptidalkoholen DD298932A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH315387		1987-08-17

Publications (1)

Publication Number	Publication Date
DD298932A5 true DD298932A5 (de)	1992-03-19

Family

ID=4249761

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88318954A DD298932A5 (de)	1987-08-17	1988-08-15	Verfahren zur herstellung von peptidalkoholen

Country Status (9)

Country	Link
BG (1)	BG60272B2 (pl)
CZ (1)	CZ281518B6 (pl)
DD (1)	DD298932A5 (pl)
FR (1)	FR2619566B1 (pl)
PL (1)	PL154068B1 (pl)
RO (1)	RO101204B (pl)
RU (1)	RU1792418C (pl)
SK (1)	SK561888A3 (pl)
YU (1)	YU48368B (pl)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4254023A (en) *	1979-10-16	1981-03-03	Pennwalt Corporation	Synthesis of peptide alcohols by the solid phase method

1987
- 1987-10-12 PL PL1987281585A patent/PL154068B1/pl unknown
1988
- 1988-03-04 FR FR8802759A patent/FR2619566B1/fr not_active Expired - Lifetime
- 1988-08-15 RO RO134904A patent/RO101204B/ro unknown
- 1988-08-15 CZ CS885618A patent/CZ281518B6/cs not_active IP Right Cessation
- 1988-08-15 YU YU157988A patent/YU48368B/sh unknown
- 1988-08-15 SK SK5618-88A patent/SK561888A3/sk unknown
- 1988-08-15 DD DD88318954A patent/DD298932A5/de not_active IP Right Cessation
- 1988-08-16 BG BG85251A patent/BG60272B2/xx unknown
- 1988-08-16 RU SU4356419A patent/RU1792418C/ru active

Also Published As

Publication number	Publication date
CZ561888A3 (en)	1996-08-14
PL154068B1 (en)	1991-06-28
RO101204B (ro)	1992-01-10
YU48368B (sh)	1998-07-10
FR2619566A1 (fr)	1989-02-24
BG60272B1 (bg)	1994-03-31
FR2619566B1 (fr)	1993-12-10
YU157988A (en)	1990-04-30
RU1792418C (ru)	1993-01-30
CZ281518B6 (cs)	1996-10-16
SK278318B6 (en)	1996-10-02
BG60272B2 (en)	1994-03-31
SK561888A3 (en)	1996-10-02

Legal Events

Date	Code	Title	Description
1995-06-08	ENJ	Ceased due to non-payment of renewal fee

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