Structural Studies of Vγ2Vδ2 T Cell Phosphoantigens

Yonghui Zhang, Yongcheng Song, Fenglin Yin, Erin Broderick, Kathryn Siegel, Amanda Goddard, Edward Nieves, Ljiljana Pasa-Tolic, Yoshimasa Tanaka, Hong Wang, Craig T. Morita, Eric Oldfield

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

Human γδ T cells containing the Vγ2Vδ2 (Vγ9Vδ2) T cell receptor are stimulated by a broad variety of small, phosphorus-containing antigenic molecules called phosphoantigens. The structures of several species present in both Mycobacteria (TUBags1-4) and in Escherichia coli have been reported to contain a formyl-alkyl diphosphate core. Here we report the synthesis of the lead member of the series, 3-formyl-1-butyl diphosphate. This compound has low activity for γδ T cell stimulation, unlike its highly active isomer (E)-4-hydroxy-3-methyl-but-2-enyl diphosphate, necessitating a revision of the structure of TUBag1. Likewise, the structure of the species identified as the pentyl analog (TUBag 2) is revised to 6-phosphogluconate. These results indicate that neither TUBag1 nor the m/e 275 species proposed for TUBag2 are 3-formyl-1-alkyl diphosphates, leading to the conclusion that none of the natural phosphoantigens (TUBags1-4) possess the structures reported previously.

Original languageEnglish (US)
Pages (from-to)985-992
Number of pages8
JournalChemistry and Biology
Volume13
Issue number9
DOIs
StatePublished - Sep 1 2006

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmacology
  • Drug Discovery
  • Clinical Biochemistry

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    Zhang, Y., Song, Y., Yin, F., Broderick, E., Siegel, K., Goddard, A., Nieves, E., Pasa-Tolic, L., Tanaka, Y., Wang, H., Morita, C. T., & Oldfield, E. (2006). Structural Studies of Vγ2Vδ2 T Cell Phosphoantigens. Chemistry and Biology, 13(9), 985-992. https://doi.org/10.1016/j.chembiol.2006.08.007