What question did this study set out to answer?

This research aims to synthesize sulfobacin A and its analogues and assess their immunological recognition by T cells.

May 7, 2026ACS Medicinal Chemistry Letters0 citations

Synthesis and Evaluation of Sulfobacin A and Analogues for Their Roles in Immunological Recognition

CCChhabi Lal ChaudharyUniversity of Kentucky PLPriscilla C. LagesUniversity of Kentucky APAngélica M. PeñaUniversity of Kentucky

Key Points

This research aims to synthesize sulfobacin A and its analogues and assess their immunological recognition by T cells.
Total synthesis of sulfobacin A and analogues via dynamic kinetic resolution
Utilized catalytic asymmetric reactions to establish three stereogenic centers
Biological evaluation using CD1 tetramers to observe T-cell recognition.
Sulfobacin A is recognized by multiple T-cell subsets including CD4, CD8, and NKT cells.
The overall yield of sulfobacin A was improved to 7.8% through late-stage optimization.
Modification of the lipid headgroup reduced CD1-mediated T-cell recognition.

Abstract

We report the total synthesis of sulfobacin A (1) and its stereoisomeric analogue 1a via dynamic kinetic resolution of racemic precursors using catalytic asymmetric reactions to establish three stereogenic centers without chiral building blocks. Late-stage optimization of the amide coupling improved the overall yield of 1 to 7.8%. Preliminary biological evaluation reveals that sulfobacin A is recognized by multiple T-cell subsets (CD4, CD8, and NKT cells) when presented by multiple CD1 tetramers, indicating that this sulfonolipid can engage T cells that influence both innate (NKT) and adaptive (CD4 and CD8) immune responses. Moreover, our data suggest that modification of the lipid headgroup or alteration to a monoacyl lipid diminishes CD1-mediated T-cell recognition.

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