N-(benzyloxycarbonyl)-O-(tert-butyl)-L-aspartyl-glycine tert-butyl ester | 475101-71-4

• 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-(benzyloxycarbonyl)-O-(tert-butyl)-L-aspartyl-glycine tert-butyl ester
• 英文别名: Z-Asp(O-t-Bu)-Gly-O-t-Bu
• CAS: 475101-71-4
• 化学式: C₂₂H₃₂N₂O₇
• 分子量: 436.505
• InChiKey: VJYOMELCJRFUPI-INIZCTEOSA-N

物化性质

• 沸点：
  601.8±55.0 °C(Predicted)
• 密度：
  1.151±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.47
• 重原子数：
  31.0
• 可旋转键数：
  8.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  120.03
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-O-(tert-butyl)-L-aspartyl-glycine tert-butyl ester 在 palladium on activated charcoal 吗啉 、 WSCD*HCl 、 氢气 、 1-羟基苯并三唑 、 溶剂黄146 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 3.0h， 生成 H-Trp(Boc)-Pro-Asp(OtBu)-Gly-OtBu
  参考文献：
  名称：

  Synthetic Approach Toward the Partial Sequences of Betaglycan in the Linkage Region on Solid Support and in Solution Phase

  摘要：

  We have synthesized, for the first time, the partial sequence of the betaglycan composed of the tetraosyl hexapeptide, which was directly usable as a probe for enzymatic glycosyl transfer. Stepwise elongation afforded the corresponding tetraosyl trichloroacetimidate. The common glycosyl dipeptide:[beta-D-GlcA-(1 -> 3)-beta-D-Gal-(1 -> 3)-beta-D-Gal-(1 -> 4)-beta-D- Xyl-(1 -> O)-Ser-Gly] was synthesized by glycosylation of the corresponding tetraosyl trichloroacetimidate and Ser-Gly moiety. The glycosyl dipeptide was coupled with other core peptide parts in solution phase and on a solid support. These glycosyl hexapeptides were then transformed into the desired target compounds.

  DOI：

  10.1080/07328300701296810
• 作为产物：
  描述：

  甘氨酸叔丁酯 、 N-苄氧羰基-L-天门冬氨酸 4-叔丁酯 在 WCSD*HCl 、 1-羟基苯并三唑 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到N-(benzyloxycarbonyl)-O-(tert-butyl)-L-aspartyl-glycine tert-butyl ester
  参考文献：
  名称：

  Synthesis of betaglycan-type tetraosyl hexapeptide: a possible precursor regulating enzymatic elongation toward heparin

  摘要：

  Tetraosyl hexapeptide, a part of the sequence of betaglycan: beta-D-GlcA-(1-->3)-beta-D-Gal-(1-->3)-beta-D-Gal-(1-->4)-beta-D-Xyl-(1-->O-SerGlyTrpProAspGly (1), which was designed as a probe for glycan elongation toward heparin, was synthesized in a stereocontrolled manner. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00327-x

文献信息

• Synthesis and activity of novel glutathione analogues containing an urethane backbone linkage
  作者：I Cacciatore、A.M Caccuri、A Di Stefano、G Luisi、M Nalli、F Pinnen、G Ricci、P Sozio

  DOI：10.1016/s0014-827x(03)00135-6

  日期：2003.9

  The new GSH analogues H-Glo(-Ser-Gly-OH)-OH (5), its O-benzyl derivative 4, and H-Glo(-Asp-Gly-OH)-OH (9), characterized by the replacement of central cysteine with either serine or aspartic acid, and containing an urethanic fragment as isosteric substitution of the scissile gamma-glutamylic junction, have been synthesized and characterized. Their ability to inhibit human GST P1-1 (hGST P1-1) in comparison

  新的GSH类似物H-Glo（-Ser-Gly-OH）-OH（5），其O-苄基衍生物4和H-Glo（-Asp-Gly-OH）-OH（9）已经合成并表征了含有丝氨酸或天冬氨酸的半胱氨酸中央半胱氨酸，并含有尿嘧啶片段作为可裂变的γ-谷氨酸连接的等位取代。与H-Glu（-Ser-Gly-OH）-OH和H-Glu（-Asp-Gly-OH）-OH相比，它们抑制人GST P1-1（hGST P1-1）的能力已经评估了大鼠GST 3-3和4-4的抑制剂。为了进一步研究等位取代对新的GSH类似物4、5和9的结合能力的影响，还对先前报道的含半胱氨酰的类似物H-Glo（-Cys-Gly-OH）-OH进行了评估。作为hGSTP1-1的共同底物。