Candida albicans β-1,2 mannosyl transferase Bmt3: Preparation and evaluation of a β (1,2), α (1,2)-tetramannosyl fluorescent substrate

• Published in: Bioorganic & medicinal chemistry Vol. 24; no. 6; pp. 1362 - 1368
• Main Authors: Cattiaux, Laurent, Mée, Anaïs, Pourcelot, Marilyne, Sfihi-Loualia, Ghenima, Hurtaux, Thomas, Maes, Emmanuel, Fradin, Chantal, Sendid, Boualem, Poulain, Daniel, Fabre, Emeline, Delplace, Florence, Guérardel, Yann, Mallet, Jean-Maurice
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 15.03.2016; Elsevier
• Subjects: Beta mannosides; Biochemistry & Molecular Biology; Candida albicans; Candida albicans - enzymology; Chemical Sciences; Chemistry; Chemistry, Medicinal; Chemistry, Organic; Fluorescent Dyes - chemistry; Fluorescent Dyes - metabolism; Fluorescent substrate; Glycosylation; Lauryl glycoside; Life Sciences & Biomedicine; Mannosides - chemistry; Mannosides - metabolism; Mannosyl transferases; Mannosyltransferases - metabolism; Mantyl; Molecular Conformation; Organic chemistry; Pharmacology & Pharmacy; Physical Sciences; Science & Technology; Substrate Specificity; Mannosyl transferases; Beta mannosides; Mantyl; Glycosylation; Fluorescent substrate; Lauryl glycoside; BETA-1,2-MANNOSYLTRANSFERASE; PATHOGENIC YEAST
• ISSN: 0968-0896; 1464-3391
• DOI: 10.1016/j.bmc.2016.02.008

[Display omitted] We describe for the first time the chemical synthesis of a tetramannoside, containing both α (1→2) and β (1→2) linkages. Dodecylthio (lauryl) glycosides were prepared from odorless dodecyl thiol and used as donors for the glycosylation steps. This tetramannoside, was coupled to a mantyl group, and revealed to be a perfect substrate of β-mannosyltransferase Bmt3, confirming the proposed specificity and allowing the preparation of a pentamannoside sequence (β Man (1,2) β Man (1,2) α Man (1,2) α Man (1,2) α Man) usable as a novel substrate for further elongation studies.