GlcNAc-β1,6-GalNAc-α1-OBn | 85054-31-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: GlcNAc-β1,6-GalNAc-α1-OBn
• 英文别名: GlcNAcβ1→6-GalNAcα-Bn；core 6-Bn；benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-α-D-galactopyranoside；GlcNAc(b1-6)GalNAc(a)-O-Bn；N-[(2R,3R,4R,5S,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-3,4-dihydroxy-6-phenylmethoxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 85054-31-5
• 化学式: C₂₃H₃₄N₂O₁₁
• 分子量: 514.53
• InChiKey: DXFWJDOYVVUWCQ-SULPZCJXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  196
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  GlcNAc-β1,6-GalNAc-α1-OBn 生成 N-[(4aR,6R,7R,8R,8aS)-6-[[(3aS,4R,6S,7R,7aR)-7-acetamido-2,2-dimethyl-6-phenylmethoxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-4-yl]methoxy]-8-hydroxy-2,2-dimethyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-7-yl]acetamide
  参考文献：
  名称：

  THOMAS, REXFORD L.;RUTAN, JAMES F.;ABBAS, SAEED A.;MATTA, KHUSHI L., CARBOHYDR. RES., 189,(1989) C. 21-30

  摘要：

  DOI：
• 作为产物：
  描述：

  benzyl 2-acetamido-3-O-acetyl-2-deoxy-α-D-galactopyranoside 在 sodium methylate 、 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 68.0h， 生成 GlcNAc-β1,6-GalNAc-α1-OBn
  参考文献：
  名称：

  苄基2-乙酰氨基-3-O-和-6-O-（2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基）-2-脱氧-α-D-吡喃半乳糖苷的合成。

  摘要：

  DOI：

  10.1016/0008-6215(83)88285-8

文献信息

• Synthetic mucin fragments. Benzyl O-β-d-galactopyranosyl-(1→3)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→6)-2-acetamido-2-deoxy-α-d-galactopyranoside and O-α-l-fucopyranosyl-(1→3)-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-(1→6)-2-acetamido-2-deoxy-d-galactopyranose
  作者：Rexford L. Thomas、James F. Rutan、Saeed A. Abbas、Khushi L. Matta

  DOI：10.1016/0008-6215(89)84083-2

  日期：1989.6

  Abstract Benzyl 2-acetamido-6- O -(2-acetamido-2-deoxy-4,6- O -isopropylidene-β- d -glucopyranosyl)-2-deoxy-3,4- O -isopropylidene-α- d - galactopyranoside ( 2 ) was obtained by acetalation of its parent disaccharide with 2,2-dimethoxypropane in hot N,N -dimethylformamide and in the presence of 4-toluenesulfonic acid. Glycosylation of 2 with 2,3,4,6-tetra- O -acetyl-α- d -galactopyranosyl bromide (catalyzed

  摘要2-乙酰氨基-6-O-（2-乙酰氨基-2-脱氧-4,6-O-异亚丙基-β-d-吡喃葡萄糖基）-2-脱氧-3,4-O-异亚丙基-α-d-在热的N，N-二甲基甲酰胺中，在4-甲苯磺酸存在下，用2，2-二甲氧基丙烷将其母体二糖乙缩醛化，得到吡喃半乳糖苷（2）。用2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物（由氰化汞催化）将2进行糖基化，然后除去保护基，得到标题三糖7。还分离出第二产物，其被鉴定为具有2-氰基丙基的7的衍生物。二缩醛2的糖基化与2,3,4-三-O-苄基-α-l-呋喃果糖基溴化物（在溴化物离子的催化下），然后系统除去保护基，得到标题三糖13。
• In situ generated O-Glycan core 1 structure as substrate for Gal(β1–3)GalNAc β-1,6-GlcNAc Transferase
  作者：Gregor Dudziak、Steffen Zeng、Eric G. Berger、Ricardo Gutiérrez Gallego、Johannis P. Kamerling、Udo Kragl、Christian Wandrey

  DOI：10.1016/s0960-894x(98)00464-8

  日期：1998.9

  beta-Galactosidase from bovine testes was used in a one pot reaction together with a recombinant beta-1,6-GlcNAc transferase for the synthesis of GlcNAc(beta 1-6)GalNAc(alpha 1-OBn) (core 6-Bn). The galactosidase, which reversibly links galactose via a (beta 1-3) linkage to N-acetylgalactosamine, provides the substrate for the GlcNAc transferase in situ. The synthesis was carried out with a yield >90%. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Optimization of the enzymatic synthesis of O -glycan core 2 structure by use of a genetic algorithm
  作者：Christoph Hoh、Gregor Dudziak、Andreas Liese

  DOI：10.1016/s0960-894x(02)00087-2

  日期：2002.4

  The enzymatic synthesis of Gal-beta1,3[GlcNAc-beta1,6]-GalNAc-alpha1-OBn (core 2-Bn) using a multi-enzyme system consisting of a beta-galactosidase (EC 3.2.1.23) from bovine testes and a recombinant core 2 beta1,6-GlcNAc transferase (C2GnT, EC 2.4.1.102) was empirically optimized by the use of a genetic algorithm. After variation of seven relevant parameters and performance of 56 experiments, two local maxima regarding the selection criterias could be found after four generations of optimization. The selectivity of core 2-Bn formation showed values up to 90%. (C) 2002 Elsevier Science Ltd. All rights reserved.