2-acetamido-3,4,6-tri-O-acetyl-1-N-<1-benzyl N-(tert-butyloxycarbonyl)-L-4-aspart-4-oyl>-2-deoxy-D-glucopyranosylamine | 78028-94-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-acetamido-3,4,6-tri-O-acetyl-1-N-<1-benzyl N-(tert-butyloxycarbonyl)-L-4-aspart-4-oyl>-2-deoxy-D-glucopyranosylamine
• 英文别名: N-[1-benzyl-N-(tert-butyloxycarbonyl)-L-aspart-4-oyl]-N-(2-acetamido-3,4,6-tri-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl) amine；benzyl N^α-tert-butoxycarbonyl-N-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-L-asparaginate；Boc-Asn(tri-O-acetyl-βGlcNAc)-OBzl；2-acetamido-3,4,6-tri-O-acetyl-1-N-[1-benzyl N-(tert-butyloxycarbonyl)-L-4-aspart-4-oyl]-2-deoxy-D-glucopyranosylamine；benzyl (2S)-4-[[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetyloxy-6-(acetyloxymethyl)oxan-2-yl]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 78028-94-1
• 化学式: C₃₀H₄₁N₃O₁₃
• 分子量: 651.668
• InChiKey: YSPLRADBFMOJHU-HSTWLWABSA-N

物化性质

• 沸点：
  829.0±65.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  46
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  211
• 氢给体数：
  3
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  2-acetamido-3,4,6-tri-O-acetyl-1-N-<1-benzyl N-(tert-butyloxycarbonyl)-L-4-aspart-4-oyl>-2-deoxy-D-glucopyranosylamine 在 palladium on activated charcoal N-甲基吗啉 、 氢气 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.13h， 生成 H-Asn(tri-O-acetyl-βGlcNAc)-Ala-OBzl*TFA
  参考文献：
  名称：

  Wong, Chi-Huey; Schuster, Matthias; Wang, Peng, Journal of the American Chemical Society, 1993, vol. 115, # 14, p. 5893 - 5898

  摘要：

  DOI：
• 作为产物：
  描述：

  3,4,6-tris-O-triethylsilyl-D-glucal 在 Raney-Ni (W-2) 吡啶 、 sodium azide 、 iodonium(di-γ-collidine) perchlorate 、 4 A molecular sieve 、 1,5-二甲氧基萘 、 氢气 、 溶剂黄146 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 维生素 C 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-acetamido-3,4,6-tri-O-acetyl-1-N-<1-benzyl N-(tert-butyloxycarbonyl)-L-4-aspart-4-oyl>-2-deoxy-D-glucopyranosylamine
  参考文献：
  名称：

  A stereoselective route from glycals to asparagine-linked N-protected glycopeptides

  摘要：

  Iodosulfonamidation of glycals followed by azidolysis produces anomerically pure 1beta-azido,2alpha-sulfonamidohexoses. Reduction of the azides, acylation of the resultant amines with an aspartic acid derivative, and deprotection of the 2-acetylamino function constitutes a completely stereospecific synthesis of asparagine-linked glycopeptide precursors from glycals.

  DOI：

  10.1021/jo00052a001

文献信息

• Chemical and enzymatic synthesis of multivalent sialoglycopeptides
  作者：Carlo Unverzagt、Soerge Kelm、James C. Paulson

  DOI：10.1016/0008-6215(94)84292-2

  日期：1994.1

  by 1H NMR and FABMS. Recombinant sialyltransferase and CMP-sialate synthetase were used for the enzymatic synthesis of sialosides on a preparative scale. The synthetic glycopeptides were tested as inhibitors of influenza virus to cells, revealing that most of the multivalent sialoglycopeptides exhibit increased binding that depends on the spacing when compared to monovalent compounds. A possible mechanism

  使用组合的化学和酶促方法已经合成了包含多个唾液酸-N-乙酰基乳糖胺侧链的直链和支链糖肽。通过遵循Boc策略的优化固相合成，可以高收率获得掺有β-GlcNAc-Asn残基的肽骨架。使用牛半乳糖基转移酶，UDP-半乳糖和小牛碱性磷酸酶破坏破坏性副产物UDP，以接近定量的产率将所得的多价糖肽半乳糖基化。随后的酶促唾液酸化产生所需的糖肽，其包含天冬酰胺连接的唾液酸-N-乙酰基乳糖胺侧链。化合物通过1 H NMR和FABMS表征。重组唾液酸转移酶和CMP-唾液酸合成酶用于制备规模的唾液酸酶的酶促合成。测试了合成糖肽作为流感病毒对细胞的抑制剂，发现与单价化合物相比，大多数多价唾液酸多肽显示结合力增加，取决于间隔。提出了增加结合的可能机制。
• Stereoselective N-Glycosylation by Staudinger Ligation
  作者：Yi He、Ronald J. Hinklin、Jiyoung Chang、Laura L. Kiessling

  DOI：10.1021/ol048271s

  日期：2004.11.1

  Stereoselective methods for the chemical synthesis of beta-N-glycosyl amides are needed to generate glycopeptides and glycoproteins. Here, we report that the Staudinger ligation can be used to form glycosylated asparagine derivatives. The reaction proceeds with high stereoselectivity, and a variety of glycosyl azides can function as substrates. Our results provide precedence for the use of this powerful

  需要化学合成β-N-糖基酰胺的立体选择方法来产生糖肽和糖蛋白。在这里，我们报告Staudinger连接可以用来形成糖基化的天冬酰胺衍生物。该反应以高的立体选择性进行，并且多种糖基叠氮化物可以用作底物。我们的结果为这种强大的酰胺键形成反应用于N-糖肽合成提供了先例。[反应：看文字]
• Synthesis of N-(β-D-glucopyranosyl)- and N-(2-acetamido-2-deoxy-β-D-glucopyranosyl) amides as inhibitors of glycogen phosphorylase
  作者：Zoltán Györgydeák、Zsuzsa Hadady、Nóra Felföldi、Attila Krakomperger、Veronika Nagy、Marietta Tóth、Attila Brunyánszki、Tibor Docsa、Pál Gergely、László Somsák

  DOI：10.1016/j.bmc.2004.07.013

  日期：2004.9

  2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl- and 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-beta-D-glucopyranosyl azides were transformed into the corresponding per-O-acetylated N-(beta-D-glycopyranosyl) amides via a PMe3 mediated Staudinger protocol (generation of N-(beta-D-glycopyranosyl)imino-trimethylphosphoranes followed by acylation with carboxylic acids, acid chlorides or anhydrides). The deprotected compounds obtained by Zemplen deacetylation were evaluated as inhibitors of rabbit muscle glycogen phosphorylase b. The best inhibitor of this series has been N-(beta-D-glucopyranosyl) 3-(2-naphthyl)-propenoic amide (K-i = 3.5 muM). (C) 2004 Elsevier Ltd. All rights reserved.
• Solid-phase synthesis of two glycopeptides containing the amino acid sequence 5 to 9 of somatostatin
  作者：Solange Lavielle、Nicolas C. Ling、Roger C. Guillemin

  DOI：10.1016/s0008-6215(00)85247-7

  日期：1981.3

  2,3,4,6-Tetra-O-acetyl-1-N-[N-(tert-butyloxycarbonyl)-L-aspart-4-oyl]-D-g lucopyranosylamine and 2-acetamido-3,4,6-tri-O-acetyl-1-N-[N-(tert-butyloxycarbonyl)-L-aspart-4-oyl]-2 -deoxy-D-glucopyranosylamine were introduced, respectively, by the solid-phase procedure in the amino acid sequence 5 to 9 of somatostatin. The two resulting glycopeptides beta-D-Glcp-(1 leads to 4)- and beta-D-GlcpNAc-(1 leads to 4)-Asn-Phe-Phe-Trp-Lys-OH were homogeneous on examination by t.l.c. and l.c., and their structures were confirmed by m.s. of the N-acetyl, permethyl derivatives.
• Amino acid fluoride for glycopeptide synthesis
  作者：Yukishige Ito、Manfred Gerz、Yoshiaki Nakahara

  DOI：10.1016/s0040-4039(99)02228-5

  日期：2000.2

  The formation of N-glycosidic linkage between N-acetylglucosamine (GlcNAc) and asparagine (Asn) was effected using aspartic acid gamma-fluoride in combination with either glycosyl azide or silyl carbamate, by the action of Lindlar catalyst or Bu4NF Further elongation of peptide chain was performed to give pentapeptide. This method was further applied into the synthesis of trisaccharidic asparagine, using beta-methoxybenzyl assisted stereoselective B-mannosylation as the key transformation. (C) 2000 Elsevier Science Ltd. All rights reserved.