Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Gal(b1-3)GalNAc(a)-O-octyl | 390400-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Gal(b1-3)GalNAc(a)-O-octyl
• 英文别名: [(2R,3S,4S,5R,6R)-6-[(2R,3R,4R,5R,6S)-5-acetamido-3-hydroxy-2-(hydroxymethyl)-6-octoxyoxan-4-yl]oxy-3,4,5-tribenzoyloxyoxan-2-yl]methyl benzoate
• CAS: 390400-39-2
• 化学式: C₅₀H₅₇NO₁₅
• 分子量: 912.0
• InChiKey: CNZBEHQRVNBGQQ-XZZFTIOQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.1
• 重原子数：
  66
• 可旋转键数：
  25
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  212
• 氢给体数：
  3
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  Chloro-acetic acid (2S,3R,4S,5S,6R)-3-acetoxy-6-acetoxymethyl-2-[(2R,3S,4R,5R,6S)-4-benzyloxy-2-benzyloxymethyl-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-6-ethylsulfanyl-tetrahydro-pyran-3-yloxy]-5-(2-chloro-acetoxy)-tetrahydro-pyran-4-yl ester 、 Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Gal(b1-3)GalNAc(a)-O-octyl 在 DMTST 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 以61%的产率得到
  参考文献：
  名称：

  Efficient synthesis of lactosaminylated core-2 O-glycans

  摘要：

  A series of lactosaminylated oligosaccharides found in mucin type O-glycans was synthesized using a generalized block strategy. The synthesis involved the addition of a protected lactosamine donor to a partially protected T-disaccharide derivative. The nonreducing galactose residues of the deblocked oligosaccharide products could be removed by beta -galactosidase from jack bean to produce the corresponding GlcNAc terminated compounds. A series of tri- to hexasaccharides was thus efficiently produced. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00550-9
• 作为产物：
  描述：

  2-乙酰氨基-2-脱氧-D-吡喃半乳糖 在 吡啶 、 sodium methylate 、 对甲苯磺酸 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 DMTST 、 三氯乙腈 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 反应 37.5h， 生成 Bz(-2)[Bz(-3)][Bz(-4)][Bz(-6)]Gal(b1-3)GalNAc(a)-O-octyl
  参考文献：
  名称：

  Efficient synthesis of lactosaminylated core-2 O-glycans

  摘要：

  A series of lactosaminylated oligosaccharides found in mucin type O-glycans was synthesized using a generalized block strategy. The synthesis involved the addition of a protected lactosamine donor to a partially protected T-disaccharide derivative. The nonreducing galactose residues of the deblocked oligosaccharide products could be removed by beta -galactosidase from jack bean to produce the corresponding GlcNAc terminated compounds. A series of tri- to hexasaccharides was thus efficiently produced. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(01)00550-9

文献信息

• Chemoenzymatic synthesis of sialylated oligosaccharides for their evaluation in a polysialyltransferase assay
  作者：Prabal Sengupta、Anup Kumar Misra、Misa Suzuki、Minoru Fukuda、Ole Hindsgaul

  DOI：10.1016/s0040-4039(03)01509-0

  日期：2003.8

  A series of sialylated β-d-Gal-(1→3)-α-d-GalNAc-octyl containing oligosaccharides representative of those found on mucin type complex O-glycans were synthesized by a chemoenzymatic approach for use in the kinetic characterization of recently cloned polysialyltransferases. Enzymatic incorporation of N-acetylneuraminic acid (sialic acid) into the synthetic acceptors was accomplished by 2,3-(N) and (

  通过化学酶法合成了一系列唾液酸化的β-d-Gal-（1→3）-α-d-GalNAc-辛基含寡糖，代表在粘蛋白型复合O-聚糖上发现的寡糖，用于近期的动力学表征克隆的聚唾液酸转移酶。的酶促掺入Ñ -acetylneuraminic氨酸（唾液酸）到合成受体是由2,3-（完成Ñ）和（ø）-sialyltransferases，得到目标化合物6 - 10在实际的产率。