ES2178204T3 - Procedimiento para la esterificacion de aminoacidos y peptidos. - Google Patents

Procedimiento para la esterificacion de aminoacidos y peptidos.

Info

Publication number
ES2178204T3
ES2178204T3 ES98917795T ES98917795T ES2178204T3 ES 2178204 T3 ES2178204 T3 ES 2178204T3 ES 98917795 T ES98917795 T ES 98917795T ES 98917795 T ES98917795 T ES 98917795T ES 2178204 T3 ES2178204 T3 ES 2178204T3
Authority
ES
Spain
Prior art keywords
amino acid
peptide
alcohol
sterification
peptides
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 - Lifetime
Application number
ES98917795T
Other languages
English (en)
Inventor
Wilhelmus Hubertus Jos Boesten
Peter Jan Leonard M Quaedflieg
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.)
Koninklijke DSM NV
Original Assignee
DSM NV
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 DSM NV filed Critical DSM NV
Application granted granted Critical
Publication of ES2178204T3 publication Critical patent/ES2178204T3/es
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06008—Dipeptides with the first amino acid being neutral
    • C07K5/06017—Dipeptides with the first amino acid being neutral and aliphatic
    • C07K5/06026—Dipeptides with the first amino acid being neutral and aliphatic the side chain containing 0 or 1 carbon atom, i.e. Gly or Ala
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
    • C07C227/18—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions involving amino or carboxyl groups, e.g. hydrolysis of esters or amides, by formation of halides, salts or esters
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C305/00—Esters of sulfuric acids
    • C07C305/02—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton
    • C07C305/04—Esters of sulfuric acids having oxygen atoms of sulfate groups bound to acyclic carbon atoms of a carbon skeleton being acyclic and saturated
    • C07C305/06—Hydrogenosulfates
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06104—Dipeptides with the first amino acid being acidic
    • C07K5/06113—Asp- or Asn-amino acid
    • C07K5/06121—Asp- or Asn-amino acid the second amino acid being aromatic or cycloaliphatic
    • C07K5/0613—Aspartame

Landscapes

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

Abstract

Procedimiento de esterificación de un aminoácido o péptido en el cual el aminoácido o péptido se convierte en el éster correspondiente en presencia de una hidrosulfato que tiene la fórmula general ROSO{sub,3}H, en la que R representa un grupo alquilo; se prepara el hidrosulfato, en presencia del aminoácido o péptido, a partir de ácido clorosulfónico y un alcohol de fórmula general ROH, en la que R tiene el mismo significado que anteriormente. La relación molar entre el ácido clorosulfónico y el aminoácido o péptido es preferiblemente de 0,8 a 2,0, en particular entre 1,0 y 1,3. El alcohol que se utiliza preferiblemente es un alcohol primario, en particular metanol. El aminoácido utilizado puede ser, por ejemplo, un {al}-aminoácido seleccionado del grupo constituido por p-hidroxifenilglicina, fenilglicina, fenilalanina, tirosina, prolina y alina; pueden utilizarse como péptido, por ejemplo, L-alanil-L-prolina o un éster de L-aspartil-L-fenilalanina.
ES98917795T 1997-04-25 1998-04-23 Procedimiento para la esterificacion de aminoacidos y peptidos. Expired - Lifetime ES2178204T3 (es)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
NL1005901A NL1005901C2 (nl) 1997-04-25 1997-04-25 Werkwijze voor de verestering van aminozuren en peptiden.

Publications (1)

Publication Number Publication Date
ES2178204T3 true ES2178204T3 (es) 2002-12-16

Family

ID=19764855

Family Applications (1)

Application Number Title Priority Date Filing Date
ES98917795T Expired - Lifetime ES2178204T3 (es) 1997-04-25 1998-04-23 Procedimiento para la esterificacion de aminoacidos y peptidos.

Country Status (8)

Country Link
US (1) US6222013B1 (es)
EP (1) EP0977726B1 (es)
JP (1) JP2001524107A (es)
AU (1) AU7085398A (es)
DE (1) DE69806747T2 (es)
ES (1) ES2178204T3 (es)
NL (1) NL1005901C2 (es)
WO (1) WO1998049133A1 (es)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1937826B1 (en) * 2005-10-20 2009-04-15 DSMIP Assets B.V. Enzymatic conversion of oligopeptide amides to oligopeptide alkyl esters
EA019536B1 (ru) * 2008-11-19 2014-04-30 ДСМ АйПи АССЕТС Б.В. Синтез пептидов с использованием энзиматической активации и конденсации
WO2011113486A1 (en) 2010-03-17 2011-09-22 Deretil, S.A. Process for the synthesis of hydroxyphenylglycine esters

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2501677A1 (fr) * 1981-03-11 1982-09-17 Flork Michel Nouveau procede d'esterification d'amino-acides
PL159729B1 (pl) * 1989-04-10 1993-01-29 Sposób wytwarzania estru metylowego kwasu 3-aminopirazynokarboksylowego-2 PL
JPH05148199A (ja) * 1991-11-28 1993-06-15 Ajinomoto Co Inc アミノ酸エステルの製造法

Also Published As

Publication number Publication date
WO1998049133A1 (en) 1998-11-05
US6222013B1 (en) 2001-04-24
DE69806747T2 (de) 2003-03-06
EP0977726B1 (en) 2002-07-24
NL1005901C2 (nl) 1998-10-27
DE69806747D1 (de) 2002-08-29
JP2001524107A (ja) 2001-11-27
AU7085398A (en) 1998-11-24
EP0977726A1 (en) 2000-02-09

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