2-acetamido-1-N--2-deoxy-β-D-glycopyranosylamine | 6216-46-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-1-N--2-deoxy-β-D-glycopyranosylamine
• 英文别名: 2-acetamido-1-N-(N-benzyloxycarbonylglycyl)-2-deoxy-β-D-glucopyranosylamine；Cbz-Gly-GlcNAc；N--2-acetamino-2-desoxy-β-D-glucopyranosylamin；N-Benzyloxycarbonylaminoacetyl-2-acetamino-2-deoxy-β-D-glucosamin；N-(N-Benzyloxycarbonyl)-2-acetamino-2-desoxy-β-D-glucopyranosylamin；benzyl N-[2-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]amino]-2-oxoethyl]carbamate
• CAS: 6216-46-2
• 化学式: C₁₈H₂₅N₃O₈
• 分子量: 411.412
• InChiKey: MRSAQJKLYHWBIO-LMHBHQSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 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 甲醇 、 palladium 10% on activated carbon 、 氢气 、 copper(II) acetate monohydrate 、 1-羟基苯并三唑 、 magnesium 作用下， 以 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.67h， 生成 2-acetamido-1-N--2-deoxy-β-D-glycopyranosylamine
  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。
• Synthesis of 2-acetamido-1-N[N-(tert-butoxycarbonyl)-l-aspart-1-oyl-(l-phenylalanyl-l-serine methyl ester)-4-oyl]-2-deoxy-β-d-glucopyranosylamine and analogs
  作者：Masahiro Tamura、Hideo Okai

  DOI：10.1016/0008-6215(84)85199-x

  日期：1984.10
• Rapid Formation of N-Glycopeptides <i>via</i> Cu(II)-Promoted Glycosylative Ligation
  作者：Ryan Joseph、Frank Brock Dyer、Philip Garner

  DOI：10.1021/ol302961s

  日期：2013.2.15

  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.