Journal article
Structural Studies of Vγ2Vδ2 T Cell Phosphoantigens
Chemistry & biology, Vol.13(9), pp.985-992
09/01/2006
DOI: 10.1016/j.chembiol.2006.08.007
PMID: 16984888
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.
Details
- Title: Subtitle
- Structural Studies of Vγ2Vδ2 T Cell Phosphoantigens
- Creators
- Yonghui ZhangYongcheng SongFenglin YinErin BroderickKathryn SiegelAmanda GoddardEdward NievesLjiljana Pasa-TolicYoshimasa TanakaHong WangCraig T MoritaEric Oldfield
- Resource Type
- Journal article
- Publication Details
- Chemistry & biology, Vol.13(9), pp.985-992
- DOI
- 10.1016/j.chembiol.2006.08.007
- PMID
- 16984888
- NLM abbreviation
- Chem Biol
- ISSN
- 1074-5521
- eISSN
- 1879-1301
- Language
- English
- Date published
- 09/01/2006
- Academic Unit
- Internal Medicine
- Record Identifier
- 9984094711102771
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