N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide | 6216-47-3

• 分子结构分类: 有机化合物
• 英文名称: N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide
• 英文别名: Cbz-Gly-Ac₃GlcNAc；N-Benzyloxycarbonylaminoacetyl-2-acetamido-2-deoxy-β-3,4,6-tri-O-acetyl-β-D-glucosamin；[(2R,3S,4R,5R,6R)-5-acetamido-3,4-diacetyloxy-6-[[2-(phenylmethoxycarbonylamino)acetyl]amino]oxan-2-yl]methyl acetate
• CAS: 6216-47-3
• 化学式: C₂₄H₃₁N₃O₁₁
• 分子量: 537.524
• InChiKey: QKUGATQRJCNDGO-OKKOYFSCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  185
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 2.0h， 生成 tert-butyl 2-[[2-[[2-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-2-oxoethyl]amino]acetyl]-(2-methylpropyl)amino]acetate
  参考文献：
  名称：

  Glycosylated peptoids as prototypical HIV-1 protease inhibitors

  摘要：

  Using a blockwise approach, N-substituted oligoglycine (NSGs) peptoids bearing N-acetylglucosamine residues in different position of the side chain were efficiently synthesized by a reiterative strategy involving mono N-alkylation and bromoacetylation. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)10028-4
• 作为产物：
  描述：

  2-乙酰氨基-3,4,6-三-O-乙酰基-2-脱氧-Β-D-吡喃葡萄糖酰基叠氮化物 在 palladium on activated charcoal 、 氢气 、 copper(II) acetate monohydrate 、 1-羟基苯并三唑 作用下， 以 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 生成 N-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-Nα-(benzyloxycarbonyl)glycineamide
  参考文献：
  名称：

  Rapid Formation of N-Glycopeptides via Cu(II)-Promoted Glycosylative Ligation

  摘要：

  Herein Is described the chemoselective Cu(II)-HOBt promoted chemical ligation of glycosylamines and peptide thioacids to give N-glycosylated peptides. The method is distinguished from other chemical approaches to peptide N-glycosylation in that (1) it can be employed In the presence of unprotected N-terminal and Lys side chain amines; (2) it Is remarkably fast, going to completion in under 30 min; and (3) It produces glycopeptides without attendant aspartimide formation.

  DOI：

  10.1021/ol302961s

文献信息

• Synthesis and biological activity of some 1-N-substituted 2-acetamido-2-deoxy-β-d-glycopyranosylamine derivatives and related analogs
  作者：Brajeswar Paul、Ralph J. Bernacki、Walter Korytnyk

  DOI：10.1016/s0008-6215(00)85318-5

  日期：——

  adenocarcinoma TA3, leukemia L1210, or leukemia P-288 cells at 1-0.01 mM concentration in vitro. Some of these derivatives were less active after O-deacetylation. Analogs of 1 in which NH2-1 was replaced by OH- or OAc-1 were also active on the same cell systems. The growth-inhibitory activity was correlated with inhibition of the incorporation of 2-amino-deoxy-D-glucose and L-leucine into a macromolecular fraction

  2-乙酰氨基-2-脱氧-3,4,6-三-O的几种1-N-取代的衍生物[卤代乙酰基，甘氨酰-，（二甲基）氨基-乙酰基，叠氮基乙酰基，三氟乙酰基和三氟甲基磺酰基-] -乙酰基-β-D-吡喃葡萄糖胺（1）被合成为细胞膜糖缀合物的潜在代谢抑制剂。在体外浓度为1-0.01 mM时，发现几种完全乙酰化的衍生物可以抑制小鼠乳腺腺癌TA3，白血病L1210或白血病P-288细胞的生长。这些衍生物中的一些在O-脱乙酰基之后活性较低。其中NH2-1被OH-或OAc-1取代的类似物1在相同的电池系统上也很活跃。生长抑制活性与2-氨基-脱氧-D-葡萄糖和L-亮氨酸掺入大分子级分的抑制有关。
• First synthesis of N-linked-glycopeptoid as new glycopeptidomimetics
  作者：Uttam K. Saha、René Roy

  DOI：10.1016/0040-4039(95)00620-r

  日期：1995.5

  The first N-linked glycopeptoid containing N-acetylglucosaminide (D-GlcNAc) was synthesized using the oligo(N-substituted glycines) (NSGs) approach. The strategy presented herein offers the advantage of a convergent synthesis.
• New Reactions of Selenocarboxylates
  作者：Spencer Knapp、Etzer Darout

  DOI：10.1021/ol047889z

  日期：2005.1.1

  By treatment with Woollins' reagent in toluene solution, carboxylic acids are converted to selenocarboxylic acids. The latter react in situ to provide new products of acid- or base-promoted substitution, addition, and amidation.