Z-Val-D-Leu-OMe | 53941-41-6

• 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: Z-Val-D-Leu-OMe
• 英文别名: methyl (2R)-4-methyl-2-[[(2S)-3-methyl-2-(phenylmethoxycarbonylamino)butanoyl]amino]pentanoate
• CAS: 53941-41-6
• 化学式: C₂₀H₃₀N₂O₅
• 分子量: 378.469
• InChiKey: PKLDYUWADSNDGB-SJORKVTESA-N

物化性质

• 沸点：
  536.1±40.0 °C(Predicted)
• 密度：
  1.101±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  甲基N-[(苄氧基)羰基]-L-缬氨酸酯	methyl (2S)-3-methyl-[(benzyloxy)carbonylamino]butanoate	24210-19-3	C14H19NO4	265.309
  CBZ-L-缬氨酸	(S)-N-(benzyloxycarbonyl)valine	1149-26-4	C13H17NO4	251.282

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	Z-Val-D-Leu-OH	53941-42-7	C19H28N2O5	364.442

反应信息

• 作为反应物：
  描述：

  Z-Val-D-Leu-OMe 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 生成 Z-Val-D-Leu-OH
  参考文献：
  名称：

  Solid phase synthesis of isariin, a long chain .BETA.-hydroxy acid-containing cyclodepsipeptide, and its diastereoisomer.

  摘要：

  应用固相合成法制备了一种含β-羟基十二烷酸的白花蛇舌草环十二肽代谢物--白花蛇舌草素（Ia）及其异构体（Ib）。以二环己基碳二亚胺（DCC）或 DCC+ 羟基琥珀酰亚胺（HOSu）为偶联剂，通过将 BOC-Val-DL-Hyd-OH、丙氨酸和 Z-Val-D-Leu-OH 相继与树脂结合的甘氨酸偶联，合成了开链去肽 H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH。从树脂裂解后，去肽通过 DCC+HOSu 环化。环化产物在 Dowex 50×4 和 Sephadex LH-20 色谱柱上色谱纯化后，通过硅胶制备型薄层色谱法成功分离，得到 Ia 和 Ib，收率适中。

  DOI：

  10.1248/cpb.22.2136
• 作为产物：
  描述：

  CBZ-L-缬氨酸 、 (R)-leucine methyl ester hydrochloride 生成 Z-Val-D-Leu-OMe
  参考文献：
  名称：

  Vicar,J. et al., Collection of Czechoslovak Chemical Communications, 1976, vol. 41, p. 3642 - 3653

  摘要：

  DOI：

文献信息

• Enzymes in organic synthesis: use of subtilisin and a highly stable mutant derived from multiple site-specific mutations
  作者：Chi Huey Wong、S. T. Chen、William J. Hennen、Jeffrey A. Bibbs、Y. F. Wang、Jennifer L. C. Liu、Michael W. Pantoliano、Marc Whitlow、Philip N. Bryan

  DOI：10.1021/ja00159a006

  日期：1990.1

  wild-type enzyme to organic synthesis has been demonstrated in the regioselective acylation of nucleosides in anhydrous dimethylformamide (with 65-100% regioselectivity at the 5'-position), in the enantioselective hydrolysis of N-protected and unprotected common and uncommon amino acid esters inmore » water (with 85-98% enantioselectivity for the L-isomer), and in the synthesis of di- and oligopeptides

  发现通过六个位点特异性突变（Met50Phe、Gly169Ala、Asn76Asp、Gln206Cys、Tyr2l7Lys 和 Asn2l8Ser）衍生自枯草杆菌蛋白酶 BPN' 的枯草杆菌蛋白酶突变体（枯草杆菌蛋白酶 8350）在水溶液中比野生溶液中的稳定性高 100 倍在无水二甲基甲酰胺中比野生型稳定 50 倍。使用酯、硫酯和酰胺底物以及过渡态类似物抑制剂 Boc-Ala-Val-Phe-CFsub 3} 的动力学研究表明，野生型和突变型酶具有非常相似的特异性和催化作用特性。野生型酶的抑制常数 (Ki = 5.0 mu}M) 是突变酶 (Ki = 1.1 mu}M) 的约 5 倍，表明突变酶与反应过渡态的结合比野生型酶。该结果与观察到的相应酯和酰胺底物的速率常数一致；即，突变体的 ksub cat}/Ksub m} 值大于野生型酶的值。突变酶和野生型酶在有机合成中的应用已在无
• Solid phase synthesis of isariin, a long chain .BETA.-hydroxy acid-containing cyclodepsipeptide, and its diastereoisomer.
  作者：KOZO OKADA、YOTARO KUROSAWA、MINORU HIRAMOTO

  DOI：10.1248/cpb.22.2136

  日期：——

  The method of solid phase synthesis was applied to the preparation of isariin (Ia), a β-hydroxydodecanoic acid-containing cyclodepsipeptide metabolite of Isaria cretacea, and its isomer (Ib). The open-chain depsipeptide, H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH, was synthesized by coupling successively BOC-Val-DL-Hyd-OH, alanine, and Z-Val-D-Leu-OH to resin-bound glycine using dicyclohexylcarbodiimide (DCC) or DCC+hydroxysuccinimide (HOSu) as coupling agent. After cleavage from the resin the depsipeptide was cyclized by means of DCC+HOSu. The cyclization product was successfully resolved, after chromatographic purification on Dowex 50×4 and Sephadex LH-20 column, by preparative thin-layer chromatography on silica gel to afford Ia and Ib in moderate yields.

  应用固相合成法制备了一种含β-羟基十二烷酸的白花蛇舌草环十二肽代谢物--白花蛇舌草素（Ia）及其异构体（Ib）。以二环己基碳二亚胺（DCC）或 DCC+ 羟基琥珀酰亚胺（HOSu）为偶联剂，通过将 BOC-Val-DL-Hyd-OH、丙氨酸和 Z-Val-D-Leu-OH 相继与树脂结合的甘氨酸偶联，合成了开链去肽 H-Val-D-Leu-Ala-Val-DL-Hyd-Gly-OH。从树脂裂解后，去肽通过 DCC+HOSu 环化。环化产物在 Dowex 50×4 和 Sephadex LH-20 色谱柱上色谱纯化后，通过硅胶制备型薄层色谱法成功分离，得到 Ia 和 Ib，收率适中。
• Synthesis and antipepsin activities of peptides having a valine or valylvaline moiety at the N-terminus.
  作者：KOZO OKADA、YOTARO KUROSAWA、SOTOO NAGAI

  DOI：10.1248/cpb.27.2163

  日期：——

  A series of peptides having a valine or valyvaline moiety at the N-terminus, 1-13, was prepared and their antipepsin activities were tested. All of the peptides possessing an N-acyl-Val-Val moiety, except one, showed some inhibitory activity against pepsin, while compounds lacking N-acyl-Val-Val showed no inhibition even at a concentration of 50 μg/ml. Compound 12, a pepstatin analog, in which a tyrosine residue is present instead of AHMHA of pepstatins, was the most potent inhibitor among the synthetic peptides, but its activity was markedly lower than that of pepstatin A. Compounds 10, 12, and 13 showed neither agonistic nor antagonistic effects on pepstatin A, suggesting major differences in binding abilities of the synthetic peptides and of pepstatin A to the enzyme. The importance of the AHMHA residue of pepstatins in relation to the inhibitory activity is discussed.

  合成了一系列在N端具有缬氨酸或二缬氨酸基团的肽，编号为1-13，并测试了它们的抗胃蛋白酶活性。所有具有N-酰基-缬-缬二肽基团的肽，除了一个，显示出一定的抑制胃蛋白酶活性，而缺乏N-酰基-缬-缬二肽基团的化合物即使在50μg/ml的浓度下也没有抑制作用。化合物12是pepstatin的类似物，其中的酪氨酸残基替代了pepstatins中的AHMHA，是合成肽中抑制作用最强的，但其活性明显低于pepstatin A。化合物10、12和13对pepstatin A既没有激动作用也没有拮抗作用，这表明合成肽和pepstatin A与酶的结合能力存在显著差异。文中讨论了pepstatins中AHMHA残基对抑制活性的重要性。
• Vicar,J. et al., Collection of Czechoslovak Chemical Communications, 1976, vol. 41, p. 3642 - 3653
  作者：Vicar,J. et al.

  DOI：——

  日期：——