PEPTIDE SYNTHESIS METHOD FOR SUPPRESSING DEFECT CAUSED BY DIKETOPIPERAZINE FORMATION

Solid-phase synthesis of a peptide has a problem that a desired elongation reaction is prevented from proceeding by diketopiperazine and a 6-membered diamine skeleton compound formed when a protective group at the N-terminal is removed. The present inventors have found that when in production of a p...

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Main Authors NOMURA, Kenichi, TAMIYA, Minoru, KANAZAWA, Junichiro, KAGE, Mirai
Format Patent
LanguageEnglish
French
German
Published 13.09.2023
Subjects
CHEMISTRY
COMBINATORIAL CHEMISTRY
LIBRARIES, e.g. CHEMICAL LIBRARIES, IN SILICOLIBRARIES
METALLURGY
ORGANIC CHEMISTRY
PEPTIDES
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Abstract Solid-phase synthesis of a peptide has a problem that a desired elongation reaction is prevented from proceeding by diketopiperazine and a 6-membered diamine skeleton compound formed when a protective group at the N-terminal is removed. The present inventors have found that when in production of a peptide by a solid-phase method, a peptide in which an amino group at the N-terminal is protected with a protective group having an Fmoc skeleton is treated in a specific solvent with a base having a pKa of 23 or more in acetonitrile as a conjugate acid, and a peptide chain is then elongated, it is possible to solve the problem described above.
AbstractList Solid-phase synthesis of a peptide has a problem that a desired elongation reaction is prevented from proceeding by diketopiperazine and a 6-membered diamine skeleton compound formed when a protective group at the N-terminal is removed. The present inventors have found that when in production of a peptide by a solid-phase method, a peptide in which an amino group at the N-terminal is protected with a protective group having an Fmoc skeleton is treated in a specific solvent with a base having a pKa of 23 or more in acetonitrile as a conjugate acid, and a peptide chain is then elongated, it is possible to solve the problem described above.
Author TAMIYA, Minoru
KAGE, Mirai
NOMURA, Kenichi
KANAZAWA, Junichiro
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DocumentTitleAlternate PEPTIDSYNTHESEVERFAHREN ZUR UNTERDRÜCKUNG VON DURCH DIKETOPIPERAZINBILDUNG VERURSACHTEN DEFEKTEN
PROCÉDÉ DE SYNTHÈSE DE PEPTIDE POUR SUPPRIMER UN DÉFAUT PROVOQUÉ PAR LA FORMATION DE DICÉTOPIPÉRAZINE
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Snippet Solid-phase synthesis of a peptide has a problem that a desired elongation reaction is prevented from proceeding by diketopiperazine and a 6-membered diamine...
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SubjectTerms CHEMISTRY
COMBINATORIAL CHEMISTRY
LIBRARIES, e.g. CHEMICAL LIBRARIES, IN SILICOLIBRARIES
METALLURGY
ORGANIC CHEMISTRY
PEPTIDES
Title PEPTIDE SYNTHESIS METHOD FOR SUPPRESSING DEFECT CAUSED BY DIKETOPIPERAZINE FORMATION
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