Gal-β1,3[GlcNAc-β1,6]-GalNAc-α1-OBn | 87866-15-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Gal-β1,3[GlcNAc-β1,6]-GalNAc-α1-OBn
• 英文别名: core-2-Bn；benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranoside；Gal(b1-3)[GlcNAc(b1-6)]GalNAc(a)-O-Bn；N-[(2R,3R,4R,5S,6R)-2-[[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-6-phenylmethoxy-4-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]methoxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]acetamide
• CAS: 87866-15-7
• 化学式: C₂₉H₄₄N₂O₁₆
• 分子量: 676.672
• InChiKey: HDGBEOJPLILRSE-YSDLGMFRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.3
• 重原子数：
  47
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  275
• 氢给体数：
  10
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  Gal-β1,3[GlcNAc-β1,6]-GalNAc-α1-OBn 在 β-galactosidase 作用下， 生成 GlcNAc-β1,6-GalNAc-α1-OBn
  参考文献：
  名称：

  Optimization of the enzymatic synthesis of O -glycan core 2 structure by use of a genetic algorithm

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(02)00087-2
• 作为产物：
  描述：

  苄基-2-乙酰胺基-2-脱氧-Alpha-D-吡喃半乳糖苷 在 β-galactosidase 作用下， 生成 Gal-β1,3[GlcNAc-β1,6]-GalNAc-α1-OBn
  参考文献：
  名称：

  Optimization of the enzymatic synthesis of O -glycan core 2 structure by use of a genetic algorithm

  摘要：

  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.

  DOI：

  10.1016/s0960-894x(02)00087-2

文献信息

• Synthetic mucin fragments: Benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-2-deoxy-3-O-β-d-galactopyranosyl-α-d-galactopyranoside and benzyl 2-acetamido-6-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-3-O-[6-O-(2-acetamido-2-deoxy-β-d-glucopyranosyl)-β- d-galactopyranosyl]-2-deoxy-α-d-galactopyranoside
  作者：Conrad F. Piskorz、Saeed A. Abbas、Khushi L. Matta

  DOI：10.1016/0008-6215(84)85130-7

  日期：1984.3

  Abstract Glycosylation of benzyl 2-acetamido-4,6- O -benzylidene-2-deoxy-α- d -galactopyranoside with 2,3,4,6-tetra- O -acetyl-α- d -galactopyranosyl bromide, catalyzed by mercuric cyanide, afforded benzyl-2-acetamido-4,6- O -benzylidene-2-deoxy-3- O -(2,3,4,6-tetra- O -acetyl-β- d -galactopyranosyl)-α- d -galactopyranoside ( 3 ). O -Deacetylation of 3 gave benzyl 2-acetamido-4,6- O -benzylidene-2-deoxy-3-

  摘要汞催化的2,3,4,6-四-O-乙酰基-α-d-吡喃半乳糖基溴化物的苄基2-乙酰氨基-4,6-O-亚苄基-2-脱氧-α-d-吡喃半乳糖苷的糖基化反应氰化物，得到苄基-2-乙酰氨基-4,6-O-亚苄基-2-脱氧-3-O-（2,3,4,6-四-O-乙酰基-β-d-吡喃半乳糖基）-α-d -半乳糖吡喃糖苷（3）。3的O-脱乙酰基化生成苄基2-乙酰氨基-4,6- O-亚苄基-2-脱氧-3- O-β-d-吡喃半乳糖苷-α-d-吡喃半乳糖苷，在与苯甲醛-氯化锌络合物缩醛化后，将所得的二亚苄基乙缩醛乙酰化，得到二糖二乙酸酯（7）。在热的80％乙酸水溶液中裂解3和7的缩醛基团，分别提供了二糖四乙酸盐（4）和二乙酸盐（8）。在甲醇钠甲醇中的8进行O-脱乙酰化，得到二糖（9）。4或8与2-甲基-（3,4,6-三-O-乙酰基-1,2-二脱氧-α-d-吡喃吡喃）-[2,1-d] -2-恶唑啉的缩合，然后O-脱
• 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.