gamma-羧基谷氨酸gamma,gamma-二-t-丁酯 | 56877-44-2

• 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
• 中文名称: gamma-羧基谷氨酸gamma,gamma-二-t-丁酯
• 英文名称: H-DL-Gla(OtBu)2-OH
• 英文别名: γ,γ'-Di-tert-butyl-DL-γ-carboxyglutamic acid；d,l-γ,γ-Di-tert-butyl-γ-carboxyglutaminsaeure；gamma-Carboxyglutamic Acid gamma,gamma-Di-t-butyl Ester；2-amino-5-[(2-methylpropan-2-yl)oxy]-4-[(2-methylpropan-2-yl)oxycarbonyl]-5-oxopentanoic acid
• CAS: 56877-44-2
• 化学式: C₁₄H₂₅NO₆
• 分子量: 303.356
• InChiKey: QGYDDDZJFUWBJQ-UHFFFAOYSA-N

物化性质

• 熔点：
  137-141°C
• 沸点：
  426.8±45.0 °C(Predicted)
• 密度：
  1.141±0.06 g/cm3(Predicted)
• 溶解度：
  可溶于二甲基亚砜、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  9
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  116
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  gamma-羧基谷氨酸gamma,gamma-二-t-丁酯 在 三氟乙酸 作用下， 生成 H-γ-羧基-DL-谷氨酸-OH
  参考文献：
  名称：

  DL-N-苄氧基羰基-γ-羧基-谷氨酸-γ，γ'-二叔丁基-α-甲基酯的制备，γ-二叔丁基-α-甲基酯是一种合适的由凝血酶原合成新的氨基三羧酸的肽衍生物。

  摘要：

  AbstractThe first synthesis of a selectively, fully protected derivative of the new aminotricarboxylic acid found in prothrombin and other homologous blood‐clotting factors, γ‐carboxy‐glutamic acid (Gla), is described. The compound DL‐N‐benzyloxycarbonyl‐γ‐carboxy‐glutamic acid γ,γ′‐di‐t‐butyl‐γ‐methyl‐ester is potentially useful for peptide synthesis. The free amino‐acid (DL‐Gla) and DL‐pyro‐γ‐carboxy‐glutamic acid dimethyl‐ester were also prepared.

  DOI：

  10.1002/hlca.19750580525
• 作为产物：
  描述：

  Z-γ,γ,-di-tert-butyl-D,L-carboxyglutamic acid methyl ester 在 palladium on activated charcoal 氢氧化钾 、 氢气 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 生成 gamma-羧基谷氨酸gamma,gamma-二-t-丁酯
  参考文献：
  名称：

  DL-N-苄氧基羰基-γ-羧基-谷氨酸-γ，γ'-二叔丁基-α-甲基酯的制备，γ-二叔丁基-α-甲基酯是一种合适的由凝血酶原合成新的氨基三羧酸的肽衍生物。

  摘要：

  AbstractThe first synthesis of a selectively, fully protected derivative of the new aminotricarboxylic acid found in prothrombin and other homologous blood‐clotting factors, γ‐carboxy‐glutamic acid (Gla), is described. The compound DL‐N‐benzyloxycarbonyl‐γ‐carboxy‐glutamic acid γ,γ′‐di‐t‐butyl‐γ‐methyl‐ester is potentially useful for peptide synthesis. The free amino‐acid (DL‐Gla) and DL‐pyro‐γ‐carboxy‐glutamic acid dimethyl‐ester were also prepared.

  DOI：

  10.1002/hlca.19750580525

文献信息

• The synthesis and properties of Gla- and Phe-containing analogues of cyclic RGD pentapeptides
  作者：John S. Davies、Christine Enjalbal、Corrine Nguyen、Loai Al-Jamri、Christian Naumer

  DOI：10.1039/b004677i

  日期：——

  Cyclopentapeptides containing the Arg-Gly-Asp motif have been synthesised using solid-phase assembly of side-chain-protected linear precursors, followed by solution-phase cyclisation. The replacement of the Asp residue by γ-carboxyglutamic acid (Gla) is a novel feature which gives rise to an analogue which inhibits cell adhesion, yet its congeners do not show activity in binding assays with recombinant integrin receptors. NMR techniques support a β/γ-turn conformation in most of the analogues.

  含有Arg-Gly-Asp基序的环五肽是通过固相合成侧链保护的线性前体，然后进行液相环化合成的。以γ-羧基谷氨酸（Gla）取代Asp残基是一项新颖的特征，这使得该类似物能够抑制细胞粘附，而其同类物在与重组整合素受体的结合实验中则未显示活性。NMR技术支持大多数类似物具有β/γ-转角构象。
• Studies on the synthesis and resolution of .gamma.-carboxyglutamic acid derivatives
  作者：Norman T. Boggs、Barry Goldsmith、R. E. Gawley、Karl A. Koehler、Richard G. Hiskey

  DOI：10.1021/jo01327a048

  日期：1979.6
• <scp>D</scp>(−)- and<scp>L</scp>(+)-γ-Carboxyglutamic Acid (Gla): Resolution of Synthetic Gla Derivatives
  作者：Walter Märki、Max Oppliger、Peter Thanei、Robert Schwyzer

  DOI：10.1002/hlca.19770600310

  日期：1977.4.20

  AbstractThe chemical resolution of γ,γ′‐di‐t‐butyl DL‐N‐benzyloxycarbonyl‐γ‐carboxy‐glutamate is described in detail (preliminary account see [1]). The D (−)‐derivative was obtained as a crystalline quinine salt, and the L (+)‐derivative as a crystalline salt with (−)‐ephedrine in yields of 44 and 70%, respectively. Physical data are indicated for the enantiomers of γ,γ′‐di‐t‐butyl N‐benzyloxycarbonyl‐γ‐carboxyglutamate, γ,γ′‐di‐t‐butyl γ‐carboxyglutamate, and γ‐carboxyglutamic acid. The absolute configurations and optical purities of the γ,γ′‐di‐t‐butyl (+)‐ and (−)‐N‐benzyloxycarbonyl‐γ‐carboxyglutamates were determined by removal of the protecting groups and decarboxylation to optically active glutamic acid.
• Kristalline Derivate des<scp>D</scp>,<scp>L</scp>-γ-Carboxyglutaminsäure-γ,γ′-di-<i>t</i>-butylesters. Vorläufige Mitteilung
  作者：Walter Märki、Max Oppliger、Robert Schwyzer

  DOI：10.1002/hlca.19760590319

  日期：1976.4.21
• Herstellung von<scp>DL</scp>-N-Benzyloxycarbonyl-γ-carboxy-glutamin-säure-γ,γ′-di-t-butyl-α-methyl-ester, einem für die Peptidsynthese geeigneten Derivat der neuen Aminotricarbonsäure aus Prothrombin
  作者：Walter Märki、Robert Schwyzer

  DOI：10.1002/hlca.19750580525

  日期：1975.7.16

  AbstractThe first synthesis of a selectively, fully protected derivative of the new aminotricarboxylic acid found in prothrombin and other homologous blood‐clotting factors, γ‐carboxy‐glutamic acid (Gla), is described. The compound DL‐N‐benzyloxycarbonyl‐γ‐carboxy‐glutamic acid γ,γ′‐di‐t‐butyl‐γ‐methyl‐ester is potentially useful for peptide synthesis. The free amino‐acid (DL‐Gla) and DL‐pyro‐γ‐carboxy‐glutamic acid dimethyl‐ester were also prepared.