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

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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 2006

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T-cells
Diphosphates
T-Lymphocytes
Mycobacterium
Isomers
Phosphorus
Molecules

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Zhang, Y., Song, Y., Yin, F., Broderick, E., Siegel, K., Goddard, A., ... 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

Structural Studies of Vγ2Vδ2 T Cell Phosphoantigens. / Zhang, Yonghui; Song, Yongcheng; Yin, Fenglin; Broderick, Erin; Siegel, Kathryn; Goddard, Amanda; Nieves, Edward; Pasa-Tolic, Ljiljana; Tanaka, Yoshimasa; Wang, Hong; Morita, Craig T.; Oldfield, Eric.

In: Chemistry and Biology, Vol. 13, No. 9, 09.2006, p. 985-992.

Research output: Contribution to journalArticle

Zhang, Y, Song, Y, Yin, F, Broderick, E, Siegel, K, Goddard, A, Nieves, E, Pasa-Tolic, L, Tanaka, Y, Wang, H, Morita, CT & Oldfield, E 2006, 'Structural Studies of Vγ2Vδ2 T Cell Phosphoantigens', Chemistry and Biology, vol. 13, no. 9, pp. 985-992. https://doi.org/10.1016/j.chembiol.2006.08.007
Zhang Y, Song Y, Yin F, Broderick E, Siegel K, Goddard A et al. Structural Studies of Vγ2Vδ2 T Cell Phosphoantigens. Chemistry and Biology. 2006 Sep;13(9):985-992. https://doi.org/10.1016/j.chembiol.2006.08.007
Zhang, Yonghui ; Song, Yongcheng ; Yin, Fenglin ; Broderick, Erin ; Siegel, Kathryn ; Goddard, Amanda ; Nieves, Edward ; Pasa-Tolic, Ljiljana ; Tanaka, Yoshimasa ; Wang, Hong ; Morita, Craig T. ; Oldfield, Eric. / Structural Studies of Vγ2Vδ2 T Cell Phosphoantigens. In: Chemistry and Biology. 2006 ; Vol. 13, No. 9. pp. 985-992.
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