δ<1-Carba,Gly⁹>vasopressin | 64156-79-2

• 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: δ<1-Carba,Gly⁹>vasopressin
• 英文别名: deamino-1-carba-vasopressin；(2S)-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]-1-[(3R,6S,9S,12S,15S)-6-(2-amino-2-oxoethyl)-9-(3-amino-3-oxopropyl)-12-benzyl-15-[(4-hydroxyphenyl)methyl]-5,8,11,14,17-pentaoxo-1-thia-4,7,10,13,16-pentazacycloicosane-3-carbonyl]pyrrolidine-2-carboxamide
• CAS: 64156-79-2
• 化学式: C₄₇H₆₆N₁₄O₁₂S
• 分子量: 1051.19
• InChiKey: MGIUPWMNCOFCIC-POFDKVPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.7
• 重原子数：
  74
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  463
• 氢给体数：
  13
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  4-nitrophenyl (2S,5S,8S,11S,14R)-11-(2-amino-2-oxoethyl)-8-(3-amino-3-oxopropyl)-5-benzyl-1-(4-(tert-butoxy)phenyl)-14-(tert-butoxycarbonyl)-2-(((2-nitrophenyl)thio)amino)-3,6,9,12-tetraoxo-16-thia-4,7,10,13-tetraazaicosan-20-oate 在 N-乙基哌啶 、 盐酸 、 氢氟酸 、 氢溴酸 、 1-羟基苯并三唑 、 苯甲醚 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.65h， 生成 δ<1-Carba,Gly⁹>vasopressin
  参考文献：
  名称：

  [7-Glycine]deamino-1-carba-vasopressin: Synthesis and pharmacological properties

  摘要：

  [8-精氨酸]去氨基-1-卡巴压素及其7-甘氨酸衍生物是通过将分子的氨基末端环状部分与羧基末端三肽酰胺进行缩合反应制备的。在第7位上将脯氨酸替换为甘氨酸会导致血管加压素样活性显著降低，而催产素样活性保持不变。

  DOI：

  10.1135/cccc19810278

文献信息

• Cysteine alkylation in unprotected peptides: synthesis of a carbavasopressin analog by intramolecular cysteine alkylation
  作者：Yat Sun Or、Richard F. Clark、Jay R. Luly

  DOI：10.1021/jo00009a040

  日期：1991.4

  An expedient method that allows modification of a cysteine residue side chain through alkylation of unprotected peptides is described. In order to test the generality of the method, an unprotected cysteine-containing tetrapeptide possessing several potentially competing nucleophilic functionalities such as amino, hydroxy, and carboxyl groups was chosen as a model peptide. The model tetrapeptide, H-Ser-Lys-Cys-Phe-OH was synthesized by standard solid-phase methods, cleaved with HF, and purified by reverse-phase HPLC. Reaction of the unprotected peptide with 1.3 equiv of various alkylating agents in saturated ammonia in methanol at 0-degrees-C proceeded cleanly to yield single alkylation products within one hour as shown by HPLC analysis. In most cases acidic, basic, and neutral side chains were introduced by this method in over 80% yield. The methodology is also applicable to the synthesis of cyclic peptides by intramolecular cysteine alkylation and provides a useful alternative to cyclizations that occur through disulfide or amine bond-forming reactions as illustrated by the synthesis of a carbavasopressin.
• OR, YAT SUN;CLARK, RICHARD F.;LULY, JAY R., J. ORG. CHEM., 56,(1991) N, C. 3146-3149
  作者：OR, YAT SUN、CLARK, RICHARD F.、LULY, JAY R.

  DOI：——

  日期：——