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KR930703345A - 펩타이드의 액상 합성법 - Google Patents

펩타이드의 액상 합성법

Info

Publication number
KR930703345A
KR930703345A KR1019930701616A KR930701616A KR930703345A KR 930703345 A KR930703345 A KR 930703345A KR 1019930701616 A KR1019930701616 A KR 1019930701616A KR 930701616 A KR930701616 A KR 930701616A KR 930703345 A KR930703345 A KR 930703345A
Authority
KR
South Korea
Prior art keywords
boc
trp
lys
phe
ala
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
KR1019930701616A
Other languages
English (en)
Inventor
스티븐슨 데이비드
Original Assignee
스튜어트 알. 슈터
스미스클라인 비참 코포레이션
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.)
Filing date
Publication date
Application filed by 스튜어트 알. 슈터, 스미스클라인 비참 코포레이션 filed Critical 스튜어트 알. 슈터
Publication of KR930703345A publication Critical patent/KR930703345A/ko
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • C07K14/575—Hormones
    • C07K14/60—Growth hormone-releasing factor [GH-RF], i.e. somatoliberin
    • 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
    • C07K1/02—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length in solution
    • 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
    • C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
    • C07K1/061—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups
    • C07K1/064—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using protecting groups for omega-amino or -guanidino functions

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

Abstract

뇌하수체 성장 호르몬 분비 활성을 갖는 펩타이드인 L-His-D-Trp-L-Trp-D-Phe-L-Lys-NH2를 제조하기 위한 액상방법을 설명한다.

Description

펩타이드의 액상 합성법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (32)

  1. a)L-Lys(BOC)-NH2를 Z-D-Phe와 결합시키고, b)Z그룹을 제거하고 생성물 D-Phe-L-Lys(BOC)-NH2를 Z-L-Trp-NH2와 결합시키고, c)Z그룹을 제거하고 생성물 L-Trp-D-Phe-L-Lys(BOC)-NH2를 Z-L-Ala와 결합시키고, d)Z그룹을 제거하고 생성물 L-Ala-L-Trp-D-Phe-L-Lys(BOC)-NH2를 Z-D-Trp와 결합시키고, e)Z그룹을 제거하고 생성물 D-Trp-L-Trp-D-Phe-L-Lys(BOC)-NH2를 (BOC)2-L-His와 결합시키고, f)BOC그룹을 제거하여 L-His-D-Trp-L-Ala-L-Trp-D-Phe-L-Lys-NH2를 수득함을 포함하는 하기식의 화합물을 제조하는 방법.
  2. L-His-D-Trp-L-Ala-L-Trp-D-Phe-L-Lys-NH2
  3. 제1항에 있어서, 중간체를 각각의 결합후에 재결정하는 방법.
  4. 제1항에 있어서, 보호그룹 Z을 촉매 가수소화분해하여 제거하는 방법.
  5. 제3항에 있어서, 촉매가 탄소상의 5% 내지 10%팔라듐인 방법.
  6. 제3항에 있어서, 촉매 가수소화분해를 대기압 내지 약100psi하에서 수행하는 방법.
  7. 제4항에 있어서, 촉매 가수소화분해를 약 100psi하에서 수행하는 방법.
  8. 제1항에 있어서, 보호그룹 BOC를 산과 카르보늄이온 스카벤저를 사용하여 제거하는 방법.
  9. 제7항에 있어서, 산이 트리플루오로아세트산이고 카르보늄이온 스카벤저가 n-프로필메르캡탄인 방법.
  10. 제1항에 있어서, 결합반응을 수용성 카르보디이미드 및 1-하이드록시-벤조트리아졸을 사용하여 수행하는 방법.
  11. 하기식의 재결정성 고체 화합물.
  12. Z-L-Lys(BOC)-NH2, 상기식에서, Z는 벤질옥시카르보닐이고, BOC는 t-부틸옥시카르보닐이다.
  13. 하기식의 재결정성 고체 화합물.
  14. Z-D-Phe-L-Lys(BOC)-NH2,상기식에서, Z는 벤질옥시카르보닐이고, BOC는 t-부틸옥시카르보닐이다.
  15. 하기식의 재결정성 고체 화합물.
  16. Z-L-Trp-D-Phe-L-Lys(BOC)-NH2, 상기식에서 Z는 벤질옥시카르보닐이고, BOC는 t-부틸옥시카르보닐이다.
  17. 하기식의 재결정성 고체 화합물.
  18. Z-L-Ala-L-Trp-D-Phe-L-Lys(BOC)-NH2, 상기식에서, Z는 벤질옥시카르보닐이고, BOC는 t-부틸옥시카르보닐이다.
  19. 하기식의 재결정성 고체 화합물.
  20. Z-D-Trp-L-Ala-L-Trp-D-Phe-L-Lys(BOC)-NH2, 상기식에서, Z는 벤질옥시카르보닐이고 BOC는 t-부틸옥시카르보닐이다.
  21. 하기식의 재결정성 고체 화합물.
  22. BOC-L-His-(BOC)-D-Trp-L-Ala-L-Trp-D-Phe-L-Lys(BOC)-NH2, 상기식에서, BOC는 t-부틸옥시카르보닐이다.
  23. D-Trp-L-Ala-L-Trp-D-Phe-L-Lys(BOC)-NH2를 BOC-L-His(BOC) 및 결합제와 반응시킴을 포함하는 하기식의 화합물의 제조방법.
  24. L-Ala-L-Trp-D-Phe-L-Lys(BOC)-NH2를 Z-D-Trp 및 결합제와 반응시킴을 포함하는 하기식의 화합물의 제조방법.
  25. Z-D-Trp-L-Ala-L-Trp-D-Phe-L-Lys(BOC)-NH2, 상기식에서, Z는 벤질옥시카르보닐이고, BOC는 t-부틸옥시카르보닐이다.
  26. L-Trp-D-Phe-L-Lys(BOC)-NH2를 Z-L-Ala 및 결합제와 반응시킴을 포함하는 하기식의 화합물의 제조방법.
  27. Z-L-Ala-L-Trp-D-Phe-L-Lys(BOC)-NH2, 상기식에서, Z는 벤질옥시카르보닐이고, BOC는 t-부틸옥시카르보닐이다.
  28. D-Phe-L-Lys(BOC)-NH2를 Z-L-Trp 및 결합제와 반응시킴을 포함하는, 하기식의 화합물의 제조방법.
  29. Z-L-Trp-D-Phe-L-Lys(BOC)-NH2, 상기식에서, Z는 벤질옥시카르보닐이고, BOC는 t-부틸옥시카르보닐이다.
  30. L-Lys(BOC)-NH2를 Z-D-Phe 및 결합제와 반응시킴을 포함하는, 하기 식의 화합물의 제조방법.
  31. Z-D-Phe-L-Lys(BOC)-NH2, 상기식에서, Z는 벤질옥시카르보닐이고, BOC는 t-부틸옥시카르보닐이다.
  32. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930701616A 1990-11-30 1991-11-25 펩타이드의 액상 합성법 Withdrawn KR930703345A (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US62109490A 1990-11-30 1990-11-30
US07/621,094 1990-11-30
PCT/US1991/008863 WO1992009620A1 (en) 1990-11-30 1991-11-25 Solution phase process for synthesis of peptide

Publications (1)

Publication Number Publication Date
KR930703345A true KR930703345A (ko) 1993-11-29

Family

ID=24488689

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019930701616A Withdrawn KR930703345A (ko) 1990-11-30 1991-11-25 펩타이드의 액상 합성법

Country Status (10)

Country Link
EP (1) EP0564587A4 (ko)
JP (1) JPH06503578A (ko)
KR (1) KR930703345A (ko)
AU (1) AU9166491A (ko)
CA (1) CA2097305A1 (ko)
IE (1) IE914157A1 (ko)
MX (1) MX9102333A (ko)
PT (1) PT99654A (ko)
WO (1) WO1992009620A1 (ko)
ZA (1) ZA919440B (ko)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP3480848B2 (ja) * 1992-06-19 2003-12-22 タカラバイオ株式会社 環状ペプチドの合成方法
GB0814519D0 (en) * 2008-08-08 2008-09-17 Imp Innovations Ltd Process

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4411890A (en) * 1981-04-14 1983-10-25 Beckman Instruments, Inc. Synthetic peptides having pituitary growth hormone releasing activity
US4105652A (en) * 1977-08-05 1978-08-08 Hoffmann-La Roche Inc. Synthesis of human β-endorphin
US4237046A (en) * 1979-04-27 1980-12-02 Miklos Bodanszky Polypeptides and methods of preparation
JPH05508859A (ja) * 1990-07-24 1993-12-09 イーストマン コダック カンパニー ペプチド合成方法

Also Published As

Publication number Publication date
PT99654A (pt) 1992-10-30
EP0564587A4 (en) 1994-08-24
ZA919440B (en) 1992-12-30
IE914157A1 (en) 1992-06-03
JPH06503578A (ja) 1994-04-21
WO1992009620A1 (en) 1992-06-11
CA2097305A1 (en) 1992-05-31
EP0564587A1 (en) 1993-10-13
MX9102333A (es) 1993-06-01
AU9166491A (en) 1992-06-25

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Legal Events

Date Code Title Description
PA0109 Patent application

Patent event code: PA01091R01D

Comment text: Patent Application

Patent event date: 19930527

PG1501 Laying open of application
PC1203 Withdrawal of no request for examination
WITN Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid