Chemical synthesis of Ser/Thr AMPylated peptides

Rwaida A. Al-Eryani, Yan Li, Haydn L. Ball

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

A method for the solid phase chemical synthesis of AMPylated Ser/Thr containing peptides is described. Peptides were phosphonylated using the H-phosphonate method, then the adenosine moiety was introduced using 2′,3′-isopropylidene adenosine and the condensing reagent PyBOP. Oxidation with iodine yielded the desired AMPylated product in good yield following acidolytic cleavage from the resin support.

Original languageEnglish (US)
Pages (from-to)1730-1731
Number of pages2
JournalTetrahedron Letters
Volume51
Issue number13
DOIs
StatePublished - Mar 31 2010

Fingerprint

Adenosine
Organophosphonates
Peptides
Solid-Phase Synthesis Techniques
Iodine
Resins
Oxidation
propylene

Keywords

  • 2′,3′-Isopropylidene adenosine
  • AMP
  • AMPylation
  • Benzotriazole-1-yl oxy-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBOP)
  • Bis(diethylamino) chlorophosphine
  • H-Phosphonate
  • SPPS

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Chemical synthesis of Ser/Thr AMPylated peptides. / Al-Eryani, Rwaida A.; Li, Yan; Ball, Haydn L.

In: Tetrahedron Letters, Vol. 51, No. 13, 31.03.2010, p. 1730-1731.

Research output: Contribution to journalArticle

Al-Eryani, Rwaida A. ; Li, Yan ; Ball, Haydn L. / Chemical synthesis of Ser/Thr AMPylated peptides. In: Tetrahedron Letters. 2010 ; Vol. 51, No. 13. pp. 1730-1731.
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