L-fucosyl_p-(α1->4)-D-N-acetylglucosaminyl_p-(β1->3)-D-galactosyl_p-(β1-O-methyl) | 116079-23-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: L-fucosyl_p-(α1->4)-D-N-acetylglucosaminyl_p-(β1->3)-D-galactosyl_p-(β1-O-methyl)
• 英文别名: methyl O-α-L-fucopyranosyl-(1->3)-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1->3)-β-D-galactopyranoside；methyl 3-O-[2-acetamido-2-deoxy-4-O-(α-L-fucopyranosyl)-β-D-glucopyranosyl]-β-D-galactopyranoside；methyl α-L-fucopyranosyl-(1->4)-2-acetamido-2-deoxy-β-D-glucopyranosyl-(1->3)-β-D-galactopyranoside；Fuc(a1-4)GlcNAc(b1-3)b-Gal1Me；N-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5R,6R)-3,5-dihydroxy-2-(hydroxymethyl)-6-methoxyoxan-4-yl]oxy-4-hydroxy-6-(hydroxymethyl)-5-[(2S,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl]acetamide
• CAS: 116079-23-3
• 化学式: C₂₁H₃₇NO₁₅
• 分子量: 543.522
• InChiKey: TYEOFBGLMQYMMQ-LCTFVBBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  37
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  246
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  N-[(2S,3R,4R,5S,6R)-2-[(2R,3R,4S,5S,6R)-2-methoxy-3,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-4-yl]oxy-5-[(2S,3S,4R,5R,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-3-yl]acetamide 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 反应 48.0h， 以87.2%的产率得到L-fucosyl_p-(α1->4)-D-N-acetylglucosaminyl_p-(β1->3)-D-galactosyl_p-(β1-O-methyl)
  参考文献：
  名称：

  异构体三糖的合成-甲基O-α-1-呋喃果糖基-（1→3、4和6）-O-（2-乙酰氨基-2-脱氧基-β-d-吡喃葡萄糖基）-（1→3）- β-d-吡喃半乳糖苷

  摘要：

  摘要将3-O-（2-乙酰氨基-4,6-O-亚苄基-2-脱氧-β-d-吡喃葡萄糖基）-2,4,6-三-O-苄基-β-d-吡喃半乳糖苷甲基化在氢化钠存在下，在N，N-二甲基甲酰胺中的苄基溴化物提供甲基3- O-（2-乙酰氨基-3- O-苄基-4,6- O-亚苄基-2-脱氧-β-d-吡喃葡萄糖基）- 2,4,6-三-O-苄基-β-d-吡喃半乳糖苷（3）。3的亚苄基的还原性开环得到甲基3-O-（2-乙酰氨基-3,6-二-O-苄基-2-脱氧-β-d-吡喃葡萄糖基）-2,4,6-三- O-苄基-β-d-吡喃半乳糖苷（4）。用热的80％乙酸水溶液裂解3，4，6-缩醛基，得到二醇（5）。分别将化合物3、4和5进行卤离子催化的2,3,4-三-O-苄基-α-1-呋喃果糖基溴的糖基化反应，生成相应的三糖衍生物，

  DOI：

  10.1016/s0008-6215(00)90841-3

文献信息

• The flexibility of the LeaLex Tumor Associated Antigen central fragment studied by systematic and stochastic searches as well as dynamic simulations
  作者：Trudy A. Jackson、Valerie Robertson、Anne Imberty、France-Isabelle Auzanneau

  DOI：10.1016/j.bmc.2009.01.020

  日期：2009.2

  The solution conformational behavior of the Tumor-Associated Carbohydrate Antigen Le(a)Le(x) central fragment: methyl alpha-L-fucopyranosyl-(1 -> 4)-2-acetamido-2-deoxy-beta-D-glucopyranosyl-(1 -> 3)-beta-D-galactopyranoside was studied using three computational methods: a rigid systematic search as implemented in Sybyl, a stochastic search as implemented in MOE2004, and dynamics simulations using the SANDER module of AMBER9. Our results illustrate the complementarity of these methods to identify energetically relevant conformations and flexible linkages. In particular, the beta-GlcNAc-(1 -> 3)-Gal linkage was shown to be extremely flexible adopting a wide range of orientations around two energy minima. The modeling results were validated by comparison of theoretical distances, derived from the simulations, with experimental measurements obtained from 1D selective ROESY buildup curves on the synthetic fragment. (c) 2009 Elsevier Ltd. All rights reserved.