(tert-butyloxycarbonyl)glycine carbamoylmethyl ester | 88830-48-2

• 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
• 英文名称: (tert-butyloxycarbonyl)glycine carbamoylmethyl ester
• 英文别名: N-BOC-Gly-CAM；Boc-Gly-CAM；(2-Amino-2-oxoethyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate；(2-amino-2-oxoethyl) 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetate
• CAS: 88830-48-2
• 化学式: C₉H₁₆N₂O₅
• mdl: MFCD24391905
• 分子量: 232.236
• InChiKey: HPRICRRLQSFCMJ-UHFFFAOYSA-N

物化性质

• 沸点：
  425.2±30.0 °C(Predicted)
• 密度：
  1.198±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.666
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (tert-butyloxycarbonyl)glycine carbamoylmethyl ester 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 1.0h， 以3.3 g的产率得到Gly-CAM
  参考文献：
  名称：

  通过结构修饰提高肽Cys-Pro酯转化为肽硫酯的速率

  摘要：

  我们先前曾报道过，含有Cys-Pro酯（CPE）部分的肽通过从N到S的酰基转移而自发地转化为肽硫酯，然后形成二酮哌嗪。为了鉴定用于形成肽硫酯的更多反应性结构，我们修饰了CPE结构，其中CPE部分中的Pro残基被N-取代的甘氨酸衍生物替代。这些肽被更快地转化成肽硫酯。或者，在CPE部分的C-末端添加氨基酸残基也加速了硫酯的形成。

  DOI：

  10.1016/j.tetlet.2013.10.121
• 作为产物：
  描述：

  BOC-甘氨酸 、 氯乙酰胺 在 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以81%的产率得到(tert-butyloxycarbonyl)glycine carbamoylmethyl ester
  参考文献：
  名称：

  关于在模型肽的合成中使用羧酰胺基甲基酯（凸轮酯）。范围和局限性

  摘要：

  证明了羧酰胺基甲基酯（CAM酯）作为用于肽合成的羧基保护基的用途。进行了趋化肽For-Met-Leu-Phe-OH的合成以及使用CAM酯作为羧基末端保护的Met-脑啡肽的合成。这些酯在酸解去除BOC N-保护基期间，Z N-保护基的氢解期间和FMOC N-保护基的去除期间显示出良好的稳定性。CAM酯可被NaOH 0.5 N或Na 2 CO 3迅速裂解。但是，当序列中存在天冬氨酸的β-苄基酯时，我们未能成功地选择性除去CAM酯。

  DOI：

  10.1016/s0040-4020(01)96451-8

文献信息

• Carboxamidomethyl esters (CAM esters) as carboxyl protecting groups.
  作者：Jean Martinez、Jeanine Laur、Bertrand Castro

  DOI：10.1016/s0040-4039(00)88401-4

  日期：1983.1

  The carboxamidomethyl esters (CAM esters) are proposed for carboxyl protection in peptide synthesis. Amino acid CAM ester derivatives were easily prepared and showed good stability in the deblocking conditions of other common protecting groups used in peptide synthesis. The CAM esters were selectively and rapidly hydrolyzed in an alcaline medium.

  提出了羧酰胺甲基酯（CAM酯）用于肽合成中的羧基保护。氨基酸CAM酯衍生物易于制备，并且在肽合成中使用的其他常见保护基团的解封条件下显示出良好的稳定性。CAM酯在碱性介质中被选择性地快速水解。
• Development of a Hypusine Reagent for Peptide Synthesis
  作者：Raymond J. Bergeron、Christian Ludin、Ralf Müller、Richard E. Smith、Phanstiel

  DOI：10.1021/jo970119z

  日期：1997.5.1

  The synthesis of a reagent that enables the incorporation of the unusual amino acid (2S,9R)hypusine (Hpu) into peptide sequences is described. The reagent, (2S,SR)-11-[(benzyloxycarbonyl)amino]-7-(carbobenzyloxy)-2- [(9-fluorenylmethoxycarbonyl)amino]-9-(tetrahydropyran-2-yloxy)- 7-azaundecanoic acid, is utilized in the synthesis of a hexapeptide containing the primary pentapeptide sequence of the eukaryotic initiation factor eIF-5A, L-Cys-L-Thr-Gly-Hpu-L-His-Gly. The reagent is shown to be effective for both solution phase and Merrifield resin synthesis.
• Synthesis and biological activity of new peptide segments of gastrin exhibiting gastrin antagonist property
  作者：Jean Martinez、Richard Magous、Marie Francoise Lignon、Jeanine Laur、Bertrand Castro、Jean Pierre Bali

  DOI：10.1021/jm00378a012

  日期：1984.12

  A series of C-terminal peptide segments of gastrin, i.e., (tert-butyloxycarbonyl)-L-tryptophyl-L-methionyl-L-aspartic acid amide, (tert-butyloxycarbonyl)-glycyl-L-tryptophyl-L-methionyl-L-aspartic acid amide, (tert-butyloxy-carbonyl)-L-tyrosyl-glycyl-L-tryptophyl-L-methionyl-L-asp artic acid amide, and (benzyloxycarbonyl)-L-glutamyl-L-alanyl-L-tyrosyl-glycyl-L-tryptophyl-L -methionyl-L-aspartic acid amide were prepared and were shown to competitively inhibit the binding of labeled human gastrin to its receptors in an isolated gastric mucosal cell preparation and to antagonize the action of gastrin on gastric acid secretion (ED50 from 1.5 to 7 mg/kg) in vivo in the reperfused rat stomach, determined according to the method of Ghosh and Schild. From these studies, it could be concluded that the C-terminal phenylalanine residue, which is of primary importance for intrinsic biological gastrin-like activity, is not essential for binding to gastrin receptors.
• On the use of carboxamidomethyl esters (cam esters) in the synthesis of model peptides. scope and limitations
  作者：Jean Martinez、Janine Laur、Bertrand Castro

  DOI：10.1016/s0040-4020(01)96451-8

  日期：1985.1

  protecting group for peptide synthesis was demonstrated. The synthesis of the chemotactic peptide For-Met-Leu-Phe-OH as well as the synthesis of Met-enkephalin using CAM ester as carboxyl terminal protection were performed. These esters showed good stability during acidolytic removal of BOC N-protecting group, during hydrogenolysis of Z N-protecting group and during removal of FMOC N-protecting group. CAM

  证明了羧酰胺基甲基酯（CAM酯）作为用于肽合成的羧基保护基的用途。进行了趋化肽For-Met-Leu-Phe-OH的合成以及使用CAM酯作为羧基末端保护的Met-脑啡肽的合成。这些酯在酸解去除BOC N-保护基期间，Z N-保护基的氢解期间和FMOC N-保护基的去除期间显示出良好的稳定性。CAM酯可被NaOH 0.5 N或Na 2 CO 3迅速裂解。但是，当序列中存在天冬氨酸的β-苄基酯时，我们未能成功地选择性除去CAM酯。
• Enhancement in the rate of conversion of peptide Cys-Pro esters to peptide thioesters by structural modification
  作者：Toru Kawakami、Akitaka Kamauchi、Emi Harada、Saburo Aimoto

  DOI：10.1016/j.tetlet.2013.10.121

  日期：2014.1

  We previously reported that the peptide containing a Cys-Pro ester (CPE) moiety is spontaneously transformed into a peptide thioester via an N to S acyl shift followed by diketopiperazine formation. In an attempt to identify more reactive structures for the formation of a peptide thioester, we modified the CPE structure, in which the Pro residue in the CPE moiety was replaced with N-substituted glycine

  我们先前曾报道过，含有Cys-Pro酯（CPE）部分的肽通过从N到S的酰基转移而自发地转化为肽硫酯，然后形成二酮哌嗪。为了鉴定用于形成肽硫酯的更多反应性结构，我们修饰了CPE结构，其中CPE部分中的Pro残基被N-取代的甘氨酸衍生物替代。这些肽被更快地转化成肽硫酯。或者，在CPE部分的C-末端添加氨基酸残基也加速了硫酯的形成。