Oxyma-based phosphates for racemization-free peptide segment couplings

Katsuhiko Mitachi, Yuki E. Kurosu, Brandon T. Hazlett, Michio Kurosu

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Glyceroacetonide-Oxyma [(2,2-dimethyl-1,3-dioxolan-4-yl)methyl 2-cyano-2-(hydroxyimino)acetate (1)] displayed remarkable physico-chemical properties as an additive for peptide-forming reactions. Although racemization-free amide-forming reactions have been established for N-urethane-protected α-amino acids with EDCI, 1, and NaHCO3 in water or DMF-water media, amide-forming reactions of N-acyl-protected α-amino acids and segment couplings of oligopeptides still require further development. Diethylphosphoryl-glyceroacetonide-oxyma (DPGOx 3) exhibits relative stability in aprotic solvents and is an effective coupling reagent for N-acyl-protected α-amino acids and oligo peptide segments. The conditions reported here is also effective in lactam-forming reactions. Unlike most of the reported coupling reagents, simple aqueous work-up procedures can remove the reagents and by-products generated in the reactions.

Original languageEnglish (US)
Pages (from-to)186-191
Number of pages6
JournalJournal of Peptide Science
Volume22
Issue number3
DOIs
StatePublished - Mar 1 2016

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Phosphates
Amino Acids
Amides
Peptides
Lactams
Oligopeptides
Water
Urethane
Chemical properties
Byproducts
Acetates
oxyma

All Science Journal Classification (ASJC) codes

  • Structural Biology
  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

Oxyma-based phosphates for racemization-free peptide segment couplings. / Mitachi, Katsuhiko; Kurosu, Yuki E.; Hazlett, Brandon T.; Kurosu, Michio.

In: Journal of Peptide Science, Vol. 22, No. 3, 01.03.2016, p. 186-191.

Research output: Contribution to journalArticle

Mitachi, Katsuhiko ; Kurosu, Yuki E. ; Hazlett, Brandon T. ; Kurosu, Michio. / Oxyma-based phosphates for racemization-free peptide segment couplings. In: Journal of Peptide Science. 2016 ; Vol. 22, No. 3. pp. 186-191.
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