GB1483500A - Acylation process - Google Patents

Acylation process

Info

Publication number
GB1483500A
GB1483500A GB5345674A GB5345674A GB1483500A GB 1483500 A GB1483500 A GB 1483500A GB 5345674 A GB5345674 A GB 5345674A GB 5345674 A GB5345674 A GB 5345674A GB 1483500 A GB1483500 A GB 1483500A
Authority
GB
United Kingdom
Prior art keywords
acid
fatty acid
protein
amino group
free amino
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
GB5345674A
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.)
Ajinomoto Co Inc
Original Assignee
Ajinomoto 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 Ajinomoto Co Inc filed Critical Ajinomoto Co Inc
Publication of GB1483500A publication Critical patent/GB1483500A/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
    • 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
    • C07K1/063—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 alpha-amino functions
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl 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
    • C07K1/06—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

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

Abstract

1483500 Acylated polypetides AJINOMOTO CO Inc 10 Dec 1974 [12 Dec 1973] 53456/74 Heading C3H [Also in Division C2] N-Higher aliphatic (C 6-22 ) acyl derivatives of free amino group-containing organic compounds are obtained by reacting a mixed acid anhydride of a higher fatty acid and sulphuric acid with a free amino group-containing organic compound in a liquid medium in the presence of a base at a temperature of from - 5‹ to 40‹ C. The mixed acid anhydride, which may be formed in situ, may be prepared by reacting 1 mole of a higher fatty acid with 1-2 moles of SO 3 or a complex thereof, for example with dioxane, DMF, dimethylaniline or pyridine at -20‹ to +40‹ C. in a non-aqueous solvent; the fatty acid starting material may be a natural or synthetic fatty acid or a metal soap or organic amine salt thereof, and the mixed anhydride product may be neutralized with an alkali or organic amine and preferably held at a temperature no higher than 20‹ C. prior to reaction with the free amino group-containing compound. The fatty acid employed may be saturated or unsaturated such as caprylic, capric, lauric, myristic, palmitic, stearic, oleic, linoleic and mixtures of fatty acids derived from natural fats and oils such as coconut, corn, olive, palm, tallow, hydrogenated tallow, soyabean and cottonseed oils. The free amino group-containing compound may be a peptide, an ester or amide thereof, or a protein such as casein, gelatin, yeast, soyabean protein, proteins separated from the squeezed serum of vegetable seed oil, proteins contained in drainage fluids obtained in fish processing, and the extracted protein of micro-organisms which are generally used in amino acid fermentation, glycyl - DL - alanine, L - lysyl - L - valine, L-lysyl-L-valine ethyl ester, glycyl-glycyl-glycine, polylysine, and peptides having an average of 2 to 12 amino acid groups which may be prepared from vegetable proteins, animal protiens such as fish protein, micro-organisms used in fermentation or yeast by partial hydrolysis with an acid, alkali or proteolytic enzyme. The preparation of hydrolysates of casein, soyabean protein and micro-organisms containing water and separated from a glutamic acid fermentation vessel, which are suitable as starting materials, is described. The products may be used as detergents, dispersing and emulsifying agents.
GB5345674A 1973-12-12 1974-12-10 Acylation process Expired GB1483500A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP13897573A JPS5141602B2 (en) 1973-12-12 1973-12-12

Publications (1)

Publication Number Publication Date
GB1483500A true GB1483500A (en) 1977-08-17

Family

ID=15234533

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5345674A Expired GB1483500A (en) 1973-12-12 1974-12-10 Acylation process

Country Status (3)

Country Link
JP (1) JPS5141602B2 (en)
FR (1) FR2254554A1 (en)
GB (1) GB1483500A (en)

Cited By (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4873087A (en) * 1982-01-14 1989-10-10 Toyo Jozo Company, Ltd. Suppository preparation having excellent absorption property
WO1990014429A1 (en) * 1989-05-25 1990-11-29 Novo Nordisk A/S An enzyme-catalyzed process for preparing n-acyl amino acids and n-acyl amino acid amides
EP0686624A1 (en) * 1994-06-07 1995-12-13 Hampshire Chemical Corporation Neutralization of N-acyl sarcosines at high shear
EP0699656A3 (en) * 1994-06-07 1996-08-21 Hampshire Chemical Corp High-temperature neutralization of N-acyl sarcosines
EP0827950A1 (en) * 1996-09-06 1998-03-11 Ajinomoto Co., Inc. Process for producing N-long-chain acyl acidic amino acids or salts thereof
US20140079642A1 (en) * 2011-01-24 2014-03-20 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd Nanoparticles based for dermal and systemic delivery of drugs
EP2842542A1 (en) 2013-08-27 2015-03-04 Evonik Industries AG A method for producing acyl amino acids
CN104649928A (en) * 2013-11-26 2015-05-27 修建东 N-capryloyl aspartate dicyclohexylamine and preparation method thereof
EP2946764A1 (en) 2014-05-23 2015-11-25 Evonik Degussa GmbH Biosynthetic production of acyl amino acids
EP3081639A1 (en) 2015-04-14 2016-10-19 Evonik Degussa GmbH Acyl amino acid production
EP3091080A1 (en) 2015-05-05 2016-11-09 Evonik Degussa GmbH Process for producing acyl amino acids employing lipases

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6257A (en) * 1985-03-19 1987-01-06 Green Cross Corp:The Amide derivative of sulfur-containing amine and fatty acid
JPS6216459A (en) * 1985-07-12 1987-01-24 Green Cross Corp:The Amide derivative of sulfur-containing amine-fatty acid
FR2705341B1 (en) * 1993-05-17 1995-06-23 Givauban Lavirotte Process for the preparation of mixtures of N-acylated amino acids, mixtures of N-acylated alpha amino acids, and their uses
FR2705673B1 (en) * 1993-05-25 1995-07-28 Givaudan Lavirotte Compositions comprising amino acid derivatives, processes for their preparation and their uses.
ES2130980B1 (en) * 1997-03-10 2000-04-01 Consejo Superior Investigacion ENZYMATIC PROCEDURE FOR THE PREPARATION OF LIPOAMINOACIDOS OF THE ALKYL AMID AND ESTER TYPE.
DE19749555A1 (en) * 1997-11-10 1999-05-12 Henkel Kgaa Enzymatically catalyzed N-acylation of amino acids, protein hydrolyzates and / or their derivatives
DE19749556A1 (en) * 1997-11-10 1999-05-12 Henkel Kgaa Enzymatically-catalyzed N-acylation of amino acids, port hydrolyzates and / or their derivatives

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4873087A (en) * 1982-01-14 1989-10-10 Toyo Jozo Company, Ltd. Suppository preparation having excellent absorption property
WO1990014429A1 (en) * 1989-05-25 1990-11-29 Novo Nordisk A/S An enzyme-catalyzed process for preparing n-acyl amino acids and n-acyl amino acid amides
EP0686624A1 (en) * 1994-06-07 1995-12-13 Hampshire Chemical Corporation Neutralization of N-acyl sarcosines at high shear
EP0699656A3 (en) * 1994-06-07 1996-08-21 Hampshire Chemical Corp High-temperature neutralization of N-acyl sarcosines
EP0827950A1 (en) * 1996-09-06 1998-03-11 Ajinomoto Co., Inc. Process for producing N-long-chain acyl acidic amino acids or salts thereof
US6008390A (en) * 1996-09-06 1999-12-28 Ajinomoto Co., Inc. Process for producing N-long-chain acyl acidic amino acids or salts thereof
US20140079642A1 (en) * 2011-01-24 2014-03-20 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd Nanoparticles based for dermal and systemic delivery of drugs
US20150374627A1 (en) * 2011-01-24 2015-12-31 Yissum Research Development Company Of The Hebrew University Of Jerusalem Ltd. Nanoparticles for dermal and systemic delivery of drugs
EP2842542A1 (en) 2013-08-27 2015-03-04 Evonik Industries AG A method for producing acyl amino acids
EP2843043A1 (en) 2013-08-27 2015-03-04 Evonik Industries AG A method for producing acyl amino acids
CN104649928A (en) * 2013-11-26 2015-05-27 修建东 N-capryloyl aspartate dicyclohexylamine and preparation method thereof
EP2946764A1 (en) 2014-05-23 2015-11-25 Evonik Degussa GmbH Biosynthetic production of acyl amino acids
EP3081639A1 (en) 2015-04-14 2016-10-19 Evonik Degussa GmbH Acyl amino acid production
EP3091080A1 (en) 2015-05-05 2016-11-09 Evonik Degussa GmbH Process for producing acyl amino acids employing lipases
WO2016177620A1 (en) 2015-05-05 2016-11-10 Evonik Degussa Gmbh Process for producing acyl amino acids employing lipases

Also Published As

Publication number Publication date
FR2254554A1 (en) 1975-07-11
JPS5141602B2 (en) 1976-11-11
JPS5088002A (en) 1975-07-15

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee