octyl 6-O-α-D-mannopyranosyl-1-thio-α-D-mannopyranoside | 166664-59-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: octyl 6-O-α-D-mannopyranosyl-1-thio-α-D-mannopyranoside
• CAS: 166664-59-1
• 化学式: C₂₀H₃₈O₁₀S
• 分子量: 470.582
• InChiKey: GBLMEEGLZJYFQT-PXGLWTFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  31.0
• 可旋转键数：
  12.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  169.3
• 氢给体数：
  7.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  octyl 6-O-α-D-mannopyranosyl-1-thio-α-D-mannopyranoside 、 Phosphoric acid (2R,3S,5R)-5-(2-amino-6-oxo-1,6-dihydro-purin-9-yl)-3-hydroxy-tetrahydro-furan-2-ylmethyl ester (2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yl ester 在 RNase α1-6 mannosyltransferase from M. smegmatis mc²155 、 MOPS buffer 作用下， 以 水 为溶剂， 反应 16.0h， 生成 、
  参考文献：
  名称：

  Synthetic mannosides act as acceptors for mycobacterial α1-6 mannosyltransferase

  摘要：

  A series of synthetic mannosides was screened in a cell-free system for their ability to act as acceptor substrates For mycobacterial mannosyltransferases. Evaluation of these compounds demonstrated the incorporation of [C-14]Man From GDP-[C-14]Man into a radiolabeled organic-soluble fraction and analysis by thin layer chromatography and autoradiography revealed the formation of two radiolabeled products. Each synthetic acceptor was capable of accepting one or two mannose residues. resulting in a major and a minor mannosylated product. Both products from each acceptor were isolated and their mass was confirmed by fast-atom bombardment-mass spectrometry (FABMS). Characterization of each mannosylated product by exo-glycosidase digestion, acetolysis and linkage analysis by gas chromatography-mass spectrometry of partially per-O-methylated alditols, revealed only alpha1-6-linked products. In addition, the antibiotic amphomycin selectively inhibited the formation of mannosylated products suggesting polyprenolmonophosphate-mannose (C-35 (50)-P-Man) was the immediate mannose donor in all mannosylation reactions observed. The ability of synthetic disaccharides to act as acceptor substrates in this system, is most Likely due to the action of a mycobacterial polyprenol-P-Man:mannan alpha1-6 mannosyltransferase involved in the biosynthesis of linear alpha1-6-linked lipomannan. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00300-x
• 作为产物：
  描述：

  octyl 1-thio-α-D-mannopyranoside 在 吡啶 、 咪唑 、 2,4,6-三甲基吡啶 、 3 A molecular sieve 、 氢氟酸 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 48.42h， 生成 octyl 6-O-α-D-mannopyranosyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal α-galactosyltransferases

  摘要：

  Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-alpha-D-mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic alpha-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MIT at 1.4, MIT at 1.2, and MIT at 1.5, respectively. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00215-7