GB986904A - Process for the production of peptides - Google Patents

Process for the production of peptides

Info

Publication number
GB986904A
GB986904A GB16273/62A GB1627362A GB986904A GB 986904 A GB986904 A GB 986904A GB 16273/62 A GB16273/62 A GB 16273/62A GB 1627362 A GB1627362 A GB 1627362A GB 986904 A GB986904 A GB 986904A
Authority
GB
United Kingdom
Prior art keywords
glycine
ethyl ester
protected
glycyl
ester
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
GB16273/62A
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of GB986904A publication Critical patent/GB986904A/en
Expired legal-status Critical Current

Links

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
    • C07K1/06—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
    • 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
    • C07K1/10—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using coupling agents
    • 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

Abstract

Peptides are prepared by condensing an amino acid or a functional derivative thereof with a b -dicarbonyl compound (the atom between the carbonyl groups being carbon), converting the carboxyl group of the product into a peptide linkage, and subjecting the product to mild acid treatment to remove the N-protecting group derived from the b -dicarbonyl compound. The amino acid may be used in the form of a salt, ester or amide, or it may itself be a peptide. The b -dicarbonyl compound may be a b -diketone, b -ketoaldehyde, b -ketoester or a b -ketoacid amide. The intermediate condensation product is an imino compound, a carbonyl oxygen being replaced by the amino acid residue, or the corresponding tautomeric enamine. In examples, (1) glycine and benzoylacetone in alcoholic KOH give the K salt of the condensation product, which is reacted with chloroacetonitrile gives the corresponding cyanomethyl ester; this is condensed with glycine ethyl ester to give N-protected glycyl-glycine which is then hydrolysed to glycyl-glycine; (2) glycine and cyclopentanone 2-carboxylic acid ethyl ester similarly give glycyl-glycine ethyl ester hydrochloride, subsequently hydrolysed to glycylglycine; (3) potassium glycine protected by benzoylacetone is reacted with glycine ethyl ester hydrochloride and dicyclohexyl-carbodiimide to produce glycyl-glycine ethyl ester protected by benzoylacetone, which is hydrolysed in two steps to glycyl-glycine; (4) similar to (3), with cyclopentan-2-one-1-carboxylic acid ethyl ester as protecting agent; 5) DL-alanine K salt protected by cyclopentan-2-one-1-carboxylic acid ethyl ester is reacted with chloroacetonitrile to give the corresponding cyanomethyl ester of the protected alanine; reaction with glycine ethyl ester gives the protected alanyl-glycine ester, which is hydrolysed to the K salt and again reacted with chloroacetonitrile and then with glycine ethyl ester; subsequent hydrolysis of the protected tripeptide gives DL-alanyl-glycyl-glycine; (6) L-alanyl-glycine is obtained similarly. Protected amino-acids and derivatives are listed and characterized.
GB16273/62A 1961-04-27 1962-04-27 Process for the production of peptides Expired GB986904A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF33780A DE1143516B (en) 1961-04-27 1961-04-27 Process for the production of peptides

Publications (1)

Publication Number Publication Date
GB986904A true GB986904A (en) 1965-03-24

Family

ID=7095247

Family Applications (1)

Application Number Title Priority Date Filing Date
GB16273/62A Expired GB986904A (en) 1961-04-27 1962-04-27 Process for the production of peptides

Country Status (4)

Country Link
BE (1) BE616915A (en)
CH (1) CH416666A (en)
DE (1) DE1143516B (en)
GB (1) GB986904A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013530948A (en) * 2010-05-17 2013-08-01 グラクソ グループ リミテッド New method

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5535059A (en) * 1978-09-05 1980-03-11 Ajinomoto Co Inc Preparation of lower alkyl ester of alpha-l-aspartyl-l- phenylalanine
FR2558471B1 (en) * 1984-01-19 1987-11-20 Isochem Sa PROCESS FOR THE PREPARATION OF ASPARTYL PEPTIDES, AND NOVEL SYNTHESIS INTERMEDIATES
ES8607216A1 (en) * 1984-01-19 1986-05-16 Isochem Sa Process for the preparation of aspartyl peptides and derivatives of aspartic acid useful in their synthesis.

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2013530948A (en) * 2010-05-17 2013-08-01 グラクソ グループ リミテッド New method
US9447052B2 (en) 2010-05-17 2016-09-20 Glaxo Group Limited Processes for preparing pyrimidine compounds
US9725420B2 (en) 2010-05-17 2017-08-08 Glaxo Group Limited Processes
EP2571857B1 (en) * 2010-05-17 2017-08-23 Glaxo Group Limited Process for the preparation of pyrimidinone compounds

Also Published As

Publication number Publication date
CH416666A (en) 1966-07-15
DE1143516B (en) 1963-02-14
BE616915A (en) 1962-10-26

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