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N-9-fluorenylmethoxycarbonylpyroglutamate. Preparation of the acid, chloride and succinimidyl ester.

Authors
  • Benoiton, N L
  • Chen, F M
Type
Published Article
Journal
International journal of peptide & protein research
Publisher
Wiley (Blackwell Publishing)
Publication Date
Apr 01, 1994
Volume
43
Issue
4
Pages
321–324
Identifiers
PMID: 8045676
Source
Medline
License
Unknown

Abstract

Fmoc-glutamic acid is converted by thionyl chloride into the dichloride, which spontaneously cyclizes to Fmoc-pyroglutamyl chloride. The latter is stable to water. Pure Fmoc-pyroglutamyl chloride is obtained by washing the reaction mixture with water, which destroys uncyclized dichloride by converting it into the 2-alkoxy-5(4H)-oxazolone that is readily hydrolyzed. Fmoc-pyroglutamic acid and succinimidyl ester are obtained from the chloride by acid hydrolysis and reaction with N-hydroxysuccinimide, respectively.

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