Lipták A, Kerékgyártó J, Szurmai Z, Duddeck H
Institute of Biochemistry, L. Kossuth University, Debrecen, Hungary.
Carbohydr Res. 1988 Apr 15;175(2):241-8. doi: 10.1016/0008-6215(88)84146-6.
The oligosaccharide core region, beta-D-Glcp-(1----3)-beta-D-Glcp-(1----4)-alpha-D-Glcp- 1----1)-alpha-D-Glcp (1), of the lipo-oligosaccharide-type antigens isolated from M. kansasii has been synthesised from 2,3,2',3',4',6'-hexa-O-benzyl-6-O-(1-phenylethyl)-alpha, alpha-trehalose (4). Compound 4 was obtained by LiAlH4-AlCl3-type hydrogenolysis of 2,3,2',3',4',6'-hexa-O-benzyl-4,6-O-(S)-(1-phenylethylidene)-alpha , alpha-trehalose. The beta-laminaribiosyl part of the molecule was built-up by sequential glycosylation steps using 2,4,6-tri-O-acetyl-3-O-allyl-alpha-D-glucopyranosyl bromide in the presence of HgBr2 and methyl 2,3,4,6-tetra-O-acetyl-1-thio-beta-D-glucopyranoside promoted by methyl triflate. The complete a priori 13C-n.m.r. spectrum assignment of 1 was achieved by applying 2D methods.
从堪萨斯分枝杆菌中分离出的脂寡糖型抗原的寡糖核心区域，即β-D-葡萄糖基-(1→3)-β-D-葡萄糖基-(1→4)-α-D-葡萄糖基-(1→1)-α-D-葡萄糖基(1)，已由2,3,2',3',4',6'-六-O-苄基-6-O-(1-苯乙基)-α,α-海藻糖(4)合成。化合物4是通过对2,3,2',3',4',6'-六-O-苄基-4,6-O-(S)-(1-苯基亚乙基)-α,α-海藻糖进行LiAlH4-AlCl3型氢解得到的。分子的β-层链二糖部分是在HgBr2存在下，使用2,4,6-三-O-乙酰基-3-O-烯丙基-α-D-吡喃葡萄糖基溴，以及在三氟甲磺酸甲酯促进下使用甲基2,3,4,6-四-O-乙酰基-1-硫代-β-D-吡喃葡萄糖苷，通过连续糖基化步骤构建而成。通过应用二维方法完成了1的完整的先验13C核磁共振谱归属。
