N-benzyloxycarbonylglycylglycylglycyne methyl ester | 13443-59-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: N-benzyloxycarbonylglycylglycylglycyne methyl ester
• 英文别名: Z-Gly-Gly-Gly-OCH3；N-benzyloxycarbonyl-glycyl=>glycyl=>-glycine methyl ester；N-Benzyloxycarbonyl-glycyl=>glycyl=>-glycin-methylester；Glycine, N-[N-[N-[(phenylmethoxy)carbonyl]glycyl]glycyl]-, methyl ester；methyl 2-[[2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]acetyl]amino]acetate
• CAS: 13443-59-9
• 化学式: C₁₅H₁₉N₃O₆
• 分子量: 337.332
• InChiKey: OAEXZMNRRDPDNH-UHFFFAOYSA-N

物化性质

• 熔点：
  151-155 °C
• 沸点：
  635.9±55.0 °C(Predicted)
• 密度：
  1.270±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  123
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-benzyloxycarbonylglycylglycylglycyne methyl ester 在 三乙胺 作用下， 以 甲醇 为溶剂， 以97.8%的产率得到3,6,9-三氧代-1-苯基-2-氧杂-4,7,10-三氮杂十二烷-12-酸
  参考文献：
  名称：

  Synthesis of N-glycopeptides and a neoglycoprotein

  摘要：

  O-(alpha-D-Glucopyranosyl)-(1----6)-O-beta-D-glucopyranosyl-(1----6)-1-N -(glycylglycylglycyl-L-seryl-L-leucyl-L-glutam-5-oyl)-alpha- D -glucopyranosylamine has been prepared, as a model of a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding L-glutamyl derivative of the trisaccharide with the pentapeptide in the presence of O,O-diethyl cyanophosphonate. Protective groups were removed by O-deacetylation, deethoxylation, and hydrogenolysis. The glutamyl derivative of the trisaccharide was also converted into the acyl azide which was condensed with bovine serum albumin to form a neoglycoprotein.

  DOI：

  10.1016/0008-6215(85)90014-x
• 作为产物：
  描述：

  methyl N-glycilglycinate 、 benzyl (2-azido-2-oxoethyl)carbamate 在 甲醇 、 乙酸乙酯 作用下， 生成 N-benzyloxycarbonylglycylglycylglycyne methyl ester
  参考文献：
  名称：

  Studies on Polypeptides. III.¹ Novel Routes to α-Amino Acid and Polypeptide Hydrazides

  摘要：

  DOI：

  10.1021/ja01122a057

文献信息

• All-Thioamidated Homo-α-Peptides: Synthesis and Conformation
  作者：Fernando Formaggio、Marco Crisma、Claudio Toniolo、Cristina Peggion

  DOI：10.1002/ejoc.201300050

  日期：2013.6

  Replacement of a peptide bond with its thioamide surrogate is a classical method for the generation of a peptidomimetic with altered spectroscopic, conformational, physicochemical, and biological properties. In this context, we synthesized short series of terminally protected homo-α-oligopeptides based on the α-amino acids Gly, Ala, and Nle, as well as their corresponding fully thioamidated analogues

  用硫代酰胺替代物替换肽键是一种经典方法，用于生成具有改变的光谱、构象、物理化学和生物学特性的肽模拟物。在这种情况下，我们基于 α-氨基酸 Gly、Ala 和 Nle 以及它们相应的完全硫代酰胺化类似物合成了短系列的末端保护的同型-α-寡肽。后一种化合物的制备是第一次通过直接硫化其氧化前体以单步方式实现。使用 X 射线衍射分析和 NMR 光谱，我们还能够确认硫代酰胺化的 α-氨基酸残基可以很容易地采用折叠或完全扩展的构象。
• US4181649A
  申请人：——

  公开号：US4181649A

  公开（公告）日：1980-01-01
• Studies on Polypeptides. III.¹ Novel Routes to α-Amino Acid and Polypeptide Hydrazides
  作者：Klaus Hofmann、Adolf Lindenmann、Margaret Z. Magee、Noorul Haq Khan

  DOI：10.1021/ja01122a057

  日期：1952.1
• Synthesis of N-glycopeptides and a neoglycoprotein
  作者：Tadahiro Takeda、Masahiko Sawaki、Yukio Ogihara、Seichi Shibata

  DOI：10.1016/0008-6215(85)90014-x

  日期：1985.6

  O-(alpha-D-Glucopyranosyl)-(1----6)-O-beta-D-glucopyranosyl-(1----6)-1-N -(glycylglycylglycyl-L-seryl-L-leucyl-L-glutam-5-oyl)-alpha- D -glucopyranosylamine has been prepared, as a model of a derivative possibly present in the glomerular basement membrane of rats, by condensation of the corresponding L-glutamyl derivative of the trisaccharide with the pentapeptide in the presence of O,O-diethyl cyanophosphonate. Protective groups were removed by O-deacetylation, deethoxylation, and hydrogenolysis. The glutamyl derivative of the trisaccharide was also converted into the acyl azide which was condensed with bovine serum albumin to form a neoglycoprotein.

表征谱图