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
École Normale Supérieure-PSL Research University, Département de Chimie, 24, rue Lhomond, 75005 Paris, France; Sorbonne Universités, UPMC Univ Paris 06, LBM, 4 place Jussieu, F-75005 Paris, France; CNRS, UMR 7203 LBM, F-75005 Paris, France.
Univ. Lille, CNRS, UMR 8576, UGSF, Unité de Glycobiologie Structurale et Fonctionnelle, F 59000 Lille, France.
Bioorg Med Chem. 2016 Mar 15;24(6):1362-8. doi: 10.1016/j.bmc.2016.02.008. Epub 2016 Feb 6.
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.
我们首次描述了一种同时含有α（1→2）和β（1→2）键的四甘露糖苷的化学合成。十二烷基硫醇（月桂基）糖苷由无臭的十二烷基硫醇制备而成，并用作糖基化步骤的供体。这种四甘露糖苷与一个甘露基连接，结果表明它是β-甘露糖基转移酶Bmt3的理想底物，证实了所提出的特异性，并使得制备一种五甘露糖序列（β Man (1,2) β Man (1,2) α Man (1,2) α Man (1,2) α Man）成为可能，该序列可用作进一步延伸研究的新型底物。
