Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi 110 007, India.
J Org Chem. 2011 Sep 16;76(18):7556-62. doi: 10.1021/jo201060t. Epub 2011 Aug 17.
A Novozyme-435 catalytic methodology has been developed for selective deacylation of one of the acyloxy functions involving a primary -OH group over the other acyloxy functions involving primary and secondary -OH groups in 4'-C-acyloxymethyl-2',3',5'-tri-O-acyl-β-D-xylofuranosyl nucleosides. Optimization of the biocatalytic reaction revealed that tetra-O-butanoyl-β-D-xylofuranosyl nucleosides are the best substrates for the enzyme. The possibility of acyl migration during enzymatic deacylation reactions has been ruled out by carrying out biocatalytic deacylation reactions on mixed esters of 4'-C-hydroxymethyl-2',3',5'-tri-O-acetyl-β-D-xylofuranosyl nucleosides. The developed methodology has been used for the efficient synthesis of xylo-LNA monomers T, U, A, and C in good yields.
已开发出一种诺维信 435 酶催化方法，用于选择性脱酰基，涉及一个伯-OH 基团的酰氧基功能之一，而涉及 4'-C-酰氧基甲基-2'、3'、5'-三-O-酰基-β-D-呋喃核苷中伯和仲-OH 基团的其他酰氧基功能。对生物催化反应的优化表明，四-O-丁酰基-β-D-呋喃核苷是该酶的最佳底物。通过对 4'-C-羟甲基-2'、3'、5'-三-O-乙酰基-β-D-呋喃核苷的混合酯进行生物催化脱酰反应，排除了酶促脱酰反应过程中酰基迁移的可能性。所开发的方法已用于高效合成 xylo-LNA 单体 T、U、A 和 C，收率良好。
