benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside | 861695-56-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside
• 英文别名: benzyl 2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS: 861695-56-9
• 化学式: C₅₅H₅₃NO₁₃
• 分子量: 936.025
• InChiKey: SPFBDCBAXAONTJ-ULFFXGJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.67
• 重原子数：
  69.0
• 可旋转键数：
  19.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  168.75
• 氢给体数：
  2.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside 、 ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1->4)-3-O-acetyl-2,6-di-O-benzoyl-1-thio-α-D-mannopyranoside 在 4 A molecular sieve 、 N-碘代丁二酰亚胺 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以95%的产率得到benzyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-3-O-acetyl-2,6-di-O-benzoyl-α-D-mannopyranosyl-(1→3)-[2,3,4,6-tetra-O-acetyl-β-Dgalactopyranosyl-(1→4)-3-O-acetyl-2,6-di-O-benzoyl-α-D-mannopyranosyl-(1→6)]-2-O-benzoyl-4-Obenzyl-β-D-mannopyranosyl-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside
  参考文献：
  名称：

  A Highly Efficient Chemoenzymatic Approach toward Glycoprotein Synthesis

  摘要：

  A highly efficient endoglycosidase-catalyzed synthesis of homogeneous glycoproteins is described. By using ribonuclease B as a model system, it was demonstrated that Endo-A could efficiently attach a preassembled oligosaccharide to a GlcNAc-containing protein in a regioand stereospecific manner, when the corresponding sugar oxazoline was used as the donor substrate. The method allows the synthesis of both natural and tailor-made N-linked glycoproteins in excellent yield.

  DOI：

  10.1021/ol061056m
• 作为产物：
  描述：

  benzyl 3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranoside 在 吡啶 、 N-碘代丁二酰亚胺 、 4 A molecular sieve 、 三氟甲磺酸二丁硼 、 硼烷 、 水 、 sodium methylate 、 silver trifluoromethanesulfonate 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 甲苯 为溶剂， 反应 22.0h， 生成 benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside
  参考文献：
  名称：

  Highly Efficient Endoglycosidase-Catalyzed Synthesis of Glycopeptides Using Oligosaccharide Oxazolines as Donor Substrates

  摘要：

  A highly efficient chemoenzymatic synthesis of N-glycopeptides was achieved. It was found that using synthetic oligosaccharide oxazolines, the mimics of the presumed oxazolinium ion intermediate formed in a retaining mechanism of substrate-assisted catalysis, as the donor substrates and GlcNAc-peptides as the acceptors, the endo-beta-N-acetylglucosaminidase (ENGase)-catalyzed transglycosylation gave a high yield (73-82%) of the corresponding glycopeptides in a regio- and stereospecific manner, regardless of the size of the peptide portions. The use of the oligosaccharide oxazolines as donor substrates not only expanded the substrate availability but also led to a substantial enhancement of the synthetic efficiency, compared to the use of natural N-glycans.

  DOI：

  10.1021/ja051715a

文献信息

• Glycopeptides of the V3 loop of gp120 and derivatives; preparation and applications as HIV-1 vaccines.
  申请人：UNIVERSITY OF MARYLAND BIOTECHNOLOGY INSTITUTE

  公开号：EP1738764A1

  公开（公告）日：2007-01-03

  A method of making a synthetic glycopeptide, by addition of a synthetic oligosaccharide oxazoline to a GlcNAc-containing peptide precursor in the presence of an enzyme selected from among Endo-A and Endo-M. In a specific implementation, the method is utilized to synthesize a trivalent V3-domain glycopeptide including three V3-domain glycopeptides on a scaffold, wherein the three V3-domain glycopeptides are arranged to mimic the V3 domain presentation in trimeric gp120. Such trivalent V3- domain glycopeptides can be utilized in a vaccine for the treatment or prevention of HIV-1 infection.

  一种合成糖肽的方法，通过在Endo-A和Endo-M中选择的酶的存在下，将合成的寡糖噁唑线加入含有GlcNAc的肽前体。在一个具体的实现中，该方法被用于合成三价V3区域糖肽，包括三个V3区域糖肽在支架上，其中三个V3区域糖肽被排列以模拟三聚体gp120中的V3区域呈现。这样的三价V3区域糖肽可以用于治疗或预防HIV-1感染的疫苗中。
• Chemoenzymatic synthesis and lectin recognition of a selectively fluorinated glycoprotein
  作者：Jared Orwenyo、Wei Huang、Lai-Xi Wang

  DOI：10.1016/j.bmc.2013.03.009

  日期：2013.8

  come from favorable hydrophobic interactions between the fluorine and a tyrosine residue in the catalytic site of the enzyme (Endo-A). SPR analysis of the binding of the fluorinated glycoproteins with lectin concanavalin A (con A) revealed the importance of the 6-hydroxyl group on the α-1,6-branched mannose moiety in con A recognition. The present study establishes a facile method for preparation of

  描述了一种用于合成选择性氟化糖蛋白的化学酶糖基化重塑方法。该方法包括氟聚糖恶唑啉的化学合成及其作为内切糖苷酶 (ENGase) 催化转糖基化为 GlcNAc 蛋白以形成均质氟糖蛋白的供体底物的用途。该方法以核糖核酸酶 B (RNase B) 的氟化糖型的合成为例。一个有趣的发现是 Man3GlcNAc 核心中 6 分支甘露糖部分的 C-6 处的氟化导致酶转糖基化中底物的反应性显着增强。结构分析表明，反应性的增强可能来自氟和酶催化位点 (Endo-A) 中的酪氨酸残基之间有利的疏水相互作用。氟化糖蛋白与凝集素伴刀豆球蛋白 A (con A) 结合的 SPR 分析揭示了 6-羟基基团在 α-1,6-支化甘露糖部分在 con A 识别中的重要性。本研究建立了一种制备选择性氟化糖蛋白的简便方法，可作为阐明特定碳水化合物-蛋白质相互作用的有价值的探针。
• GLYCOPROTEIN SYNTHESIS AND REMODELING BY ENZYMATIC TRANSGLYCOSYLATION
  申请人：University Of Maryland, Baltimore

  公开号：EP2001358B1

  公开（公告）日：2016-07-13