title: Two-step synthesis of the immunogenic bacterial glycolipid BbGL1.
abstract: Chemical synthesis of a bacterial glycolipid BbGL1 is reported in two steps starting from per-O-TMS D-galactose. The key features are glycosyl iodide mediated beta-stereoselective glycosylation in the absence of neighboring group participation and regioselective acylation.
authors.affiliation: University of California, Davis, Department of Chemistry, One Shields Avenue, Davis, California 95616, USA.
authors.forename: Suvarn S
authors.initials: SS
authors.lastname: Kulkarni
authors.forename: Jacquelyn
authors.initials: J
authors.lastname: Gervay-Hague
mesh_terms: D025065:Borrelia burgdorferi / Q000737:chemistry* / Q000276:immunology; D002784:Cholesterol / Q000737:chemistry; D005690:Galactose / Q000737:chemistry; D006017:Glycolipids / Q000138:chemical synthesis* / Q000737:chemistry / Q000276:immunology*; D006031:Glycosylation; D007211:Indoles / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D006017:Glycolipids; D007211:Indoles; D002784:Cholesterol; D005690:Galactose
references.citation: Proc Natl Acad Sci U S A. 2003 Jun 24;100(13):7913-8
references.pmid: 12799465
references.citation: J Biol Chem. 2003 Sep 5;278(36):33645-53
references.pmid: 12810705
references.citation: Org Lett. 2001 Jun 28;3(13):2081-4
references.pmid: 11418054
references.citation: Carbohydr Res. 2005 Sep 5;340(12):2052-4
references.pmid: 16023624
references.citation: Org Lett. 2002 Jun 13;4(12):2039-42
references.pmid: 12049512
references.citation: J Am Chem Soc. 2007 Jul 25;129(29):9222-35
references.pmid: 17602482
references.citation: Org Lett. 2006 Dec 7;8(25):5765-8
references.pmid: 17134267
references.citation: Carbohydr Res. 2002 Nov 19;337(21-23):1953-65
references.pmid: 12433461
references.citation: Org Lett. 2005 May 12;7(10):2063-5
references.pmid: 15876055
references.citation: Proc Natl Acad Sci U S A. 2005 Feb 1;102(5):1351-6
references.pmid: 15665086
references.citation: Carbohydr Res. 2007 Feb 26;342(3-4):621-6
references.pmid: 17182019
references.citation: Chem Commun (Camb). 2007 Jun 21;(23):2336-8
references.pmid: 17844738
references.citation: Org Lett. 2007 Apr 12;9(8):1573-6
references.pmid: 17358075
references.citation: Biochimie. 2001 Jul;83(7):683-92
references.pmid: 11522398