GB1253321A - Process for protecting mercapto groups - Google Patents

Process for protecting mercapto groups

Info

Publication number
GB1253321A
GB1253321A GB6101269A GB6101269A GB1253321A GB 1253321 A GB1253321 A GB 1253321A GB 6101269 A GB6101269 A GB 6101269A GB 6101269 A GB6101269 A GB 6101269A GB 1253321 A GB1253321 A GB 1253321A
Authority
GB
United Kingdom
Prior art keywords
cysteine
group
cooh
synthesis
acetamidomethylcysteine
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.)
Expired
Application number
GB6101269A
Inventor
Sandor Lajos Varga
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Merck and Co Inc
Original Assignee
Merck and Co Inc
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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of GB1253321A publication Critical patent/GB1253321A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D263/44—Two oxygen atoms
    • 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
    • C07K1/067—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 sulfur-containing functions

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1,253,321. Mercapto group protection. MERCK & CO. Inc. 15 Dec., 1969 [19 Dec., 1968], No. 61012/69. Heading C2C. [Also in Division C3] Mercapto groups of cysteine or cysteinecontaining peptides are protected by a R.CONHCH 2 - group (where R is alkyl or aryl) by reaction with an N-hydroxy-methylalkyl amide or an N-hydroxyarylamide in the presence of an anhydrous acid e.g. HF, F 3 C.COOH, Cl 3 C.COOH or Cl 2 CH.COOH. The blocked cysteine or cysteine containing peptide may be used as a reactant in a peptide synthesis e.g. in a synthesis of oxytocin. The -SH group is liberated by treatment of the blocked group with a water-soluble heavy metal salt or an organo metallic salt of a heavy metal. The following intermediates used in a synthesis of oxytocin: S-acetamidomethylcysteine-N- carboxyanhydride, BOC-(S-acetamidomethyl)cysteine and its hydroxy succinimide ester are prepared from S-acetamidomethylcysteine.
GB6101269A 1968-12-19 1969-12-15 Process for protecting mercapto groups Expired GB1253321A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US78540268A 1968-12-19 1968-12-19

Publications (1)

Publication Number Publication Date
GB1253321A true GB1253321A (en) 1971-11-10

Family

ID=25135403

Family Applications (1)

Application Number Title Priority Date Filing Date
GB6101269A Expired GB1253321A (en) 1968-12-19 1969-12-15 Process for protecting mercapto groups

Country Status (6)

Country Link
BR (1) BR6914672D0 (en)
CH (1) CH526517A (en)
DE (1) DE1963308A1 (en)
FR (1) FR2026554A1 (en)
GB (1) GB1253321A (en)
NL (1) NL6918030A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109160891A (en) * 2018-09-14 2019-01-08 成都市科隆化学品有限公司 A kind of Fmoc-Cys(Acm)-OH preparation method

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109160891A (en) * 2018-09-14 2019-01-08 成都市科隆化学品有限公司 A kind of Fmoc-Cys(Acm)-OH preparation method

Also Published As

Publication number Publication date
FR2026554A1 (en) 1970-09-18
CH526517A (en) 1972-08-15
BR6914672D0 (en) 1973-05-24
NL6918030A (en) 1970-06-23
DE1963308A1 (en) 1970-07-09

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