Synthesis of octyl arabinofuranosides as substrates for mycobacterial arabinosyltransferases.
A panel of octyl oligosaccharides comprised of arabinofuranose rings have been synthesized via efficient and readily scaleable routes. The key glycosylation reactions involved the coupling of octyl glycoside acceptors with the appropriate thioglycosides using N-iodosuccinimide and silver triflate activation. These syntheses were undertaken to provide substrates suitable for use in assays of mycobacterial arabinosyltransferases.
Han
Jeongseok
J
Department of Chemistry, The Ohio State University, 100 West 18th Avenue, 43210, Columbus, OH, USA.
Gadikota
Rajendrakumar Reddy
RR
McCarren
Patrick R
PR
Lowary
Todd L
TL
D001089:Arabinose / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D002236:Carbohydrate Conformation; D002240:Carbohydrate Sequence; D002384:Catalysis; D002473:Cell Wall / Q000737:chemistry; D003500:Cyclization; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D008070:Lipopolysaccharides / Q000378:metabolism; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000201:enzymology*; D009844:Oligosaccharides / Q000138:chemical synthesis / Q000737:chemistry / Q000378:metabolism; D010430:Pentosyltransferases / Q000378:metabolism*; D013237:Stereoisomerism; D013379:Substrate Specificity
D006027:Glycosides; D008070:Lipopolysaccharides; D009844:Oligosaccharides; C431714:arabinofuranose; D001089:Arabinose; D010430:Pentosyltransferases; C101967:arabinosyltransferase