title: Expeditious synthesis of Mycobacterium tuberculosis sulfolipids SL-1 and Ac2SGL analogues.
abstract: M. tuberculosis sulfoglycolipids SL-1 and Ac2SGL are highly immunogenic and potential vaccine candidates. A short and efficient methodology is reported for the synthesis of SL-1 and Ac2SGL analogues via regioselective functionalization of α,α-D-trehalose employing a highly regioselective late stage sulfation, as a key step. The SL-1 analogues 3a and 4 were obtained in 10 and 9 steps in 13.4% and 23.9% overall yields, respectively. The Ac2SGL analogue 5 was synthesized in 5 steps in 18.4% yield.
authors.affiliation: Department of Chemistry, Indian Institute of Technology Bombay , Powai, Mumbai 400076, India.
authors.forename: Vikram A
authors.initials: VA
authors.lastname: Sarpe
authors.forename: Suvarn S
authors.initials: SS
authors.lastname: Kulkarni
mesh_terms: D001428:Bacterial Vaccines / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology*; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology*; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000737:chemistry* / Q000276:immunology*; D014199:Trehalose / Q000031:analogs & derivatives / Q000737:chemistry*; D037521:Virulence Factors / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology
chemical_list: D001428:Bacterial Vaccines; D006017:Glycolipids; D037521:Virulence Factors; C011117:sulfoglycolipids; C009355:sulfolipid I; D014199:Trehalose