Z-Thr-Leu-OMe | 31025-12-4

• 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: Z-Thr-Leu-OMe
• 英文别名: methyl (2S)-2-[[(2S,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoyl]amino]-4-methylpentanoate
• CAS: 31025-12-4
• 化学式: C₁₉H₂₈N₂O₆
• 分子量: 380.441
• InChiKey: QVSDMMHBKBWPHF-KBMXLJTQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Z-Thr-Leu-OMe 在 ruthenium trichloride 、 sodium periodate 作用下， 以 四氯化碳 、 水 、 乙腈 为溶剂， 反应 1.5h， 以86%的产率得到Z-NH-CO-CO-Leu-OMe
  参考文献：
  名称：

  C-末端丝氨酸和苏氨酸延伸前体转化为 C-末端 α-酰胺化肽：垂体酶α-酰胺化作用的可能化学模型

  摘要：

  此处介绍的化学模型为从 C 端 Ser/Thr 扩展前体制备 C 端酰胺提供了一种温和实用的方法。此外，源自 N 末端和非末端 Ser/Thr 肽的草酰胺构成了一类全新的肽类似物，具有扩展的平面双肽区域，其构象和反应性特征的研究将证明是有趣的

  DOI：

  10.1021/ja00003a048
• 作为产物：
  描述：

  L-亮氨酸甲酯盐酸盐 在 C₁₂H₆B₂Br₄O₃ 、 sodium carbonate 作用下， 以 二氯甲烷 、 水 、 1,2-二氯乙烷 为溶剂， 反应 24.08h， 生成 Z-Thr-Leu-OMe
  参考文献：
  名称：

  通过催化羟基导向肽键形成简明合成 2,5-二酮哌嗪

  摘要：

  具有羟甲基官能团的 2,5-二酮哌嗪 (DKP) 是许多生物活性分子和功能材料中的必需结构。我们已经建立了一个简单的协议，用于通过二硼酸酐催化的羟基定向肽键形成简明合成此类 DKP。本报告中的连续反应由三个步骤组成，其中水是唯一的副产物的分子间催化缩合反应、氮保护基团的简单脱保护和分子内环化，使功能化 DKPs 的合成成为可能。无需任何中间纯化即可获得优异的产量。该协议的效用已通过合成天然产物、phomamide 和 Cyclo(Deala- l -Leu) 得到证明。

  DOI：

  10.1021/acs.joc.3c00195

文献信息

• Bromelain Catalyzed Synthesis of Peptides in Organic Solvent
  作者：Dar-Fu Tai、Shu-Lin Fu

  DOI：10.1002/jccs.200300025

  日期：2003.2

  exported by Taiwan. There is no deficiency for thesource of this enzyme. Therefore, the application of bro-melain to catalyze the synthesis of peptides has great poten-tial and economic value.No research effort has ever been made in peptide syn-thesis using bromelain except for catalyzing polymerizationin aqueous solution.

  是一种来自菠萝茎提取物的硫醇蛋白酶。菠萝是台湾丰富的资源。菠萝蛋白酶（EC.3,4,4,24）是台湾出口的两种主要酶之一。这种酶的来源没有缺陷。因此，将菠萝蛋白酶应用于催化多肽合成具有巨大的潜力和经济价值。除在水溶液中催化聚合外，目前还没有利用菠萝蛋白酶合成多肽的研究成果。
• The Structure of Viscosin, A Peptide Antibiotic. II. Syntheses of D-and L-3-Hydroxyacylhexapeptides including the Proposed Structure of Viscosin and Its Optical Isomers
  作者：MINORU HIRAMOTO、KOZO OKADA、SOTOO NAGAI

  DOI：10.1248/cpb.19.1315

  日期：——

  Homologs of D- and L-3-hydroxyacylhexapeptide including compound (I-1c) and its optical isomers (I-1'c, I-2c, I-2'c) were synthesized by condensing the tripeptide subunit with the dipeptide subunit followed by azide coupling of the resulting pentapeptide with D-or L-3-hydroxyacylleucine, and their antibacterial properties were examined. None of the synthetic acylhexapeptides was identical with viscosin in both physical and chemical properties and antituberculous activity.

  通过将三肽亚基与二肽亚基缩合，然后将得到的五肽与 D-或 L-3-羟乙基亮氨酸叠氮偶联，合成了 D-和 L-3-羟乙基六肽的同系物，包括化合物（I-1c）及其光学异构体（I-1'c、I-2c、I-2'c），并考察了它们的抗菌特性。合成的酰基六肽在理化性质和抗结核活性方面都与粘多糖没有相同之处。
• Protein Backbone Modification by Novel C.alpha.-C Side-Chain Scission
  作者：Darshan Ranganathan、Narendra K. Vaish、Kavita Shah

  DOI：10.1021/ja00094a008

  日期：1994.7

  alpha-Ketoamide (-NH-CO-CO-) units in intact peptides are generated from Ser/Thr residues via Ru(VIII)catalyzed C-alpha-C side-chain scission. Facets associated with this novel cu-carbon modification have been probed with 75 peptides chosen to represent every possible peptide environment. The reactions were carried out at room temperature with in situ generated Ru(VIII) in biphasic (CH3CN/CCl4/pH 3 phosphate buffer, 1:1:2 v/v) medium. Whereas Ser/Thr residues placed at the C-terminal end in peptides undergo N-C bond scission leading to des-Ser/Thr peptide amides-thus acting as Gly equivalents in simulating the alpha-amidating action of pituitary enzymes-those located at the N-terminal or nonterminal or even at the C-terminal position (protected as amide) were found to undergo oxidative C-C bond scission (involving C-alpha and C side-chain bond), resulting in the generation of alpha-ketoamide (-NH-CO-CO-) units in the intact peptide backbone. The difference in the products arising from C-alpha-C side-chain scission of Ser/Thr esters and amides is rationalized on the basis of a common mechanism involving either oxaloesters [Pep-NH-CO-COX; X = OMe] or oxalamides [X = NH2 or NH-Pep] arising from the oxidation of initially formed carbinolamide intermediates [Pep-NH-CH(OH)-COX],wherein, while the former are shown to undergo hydrolysis to terminal amides [Pep-NH2], the oxalamides are found to be stable to hydrolysis. Ancillary noteworthy findings are those of peptide bond scission when contiguous Ser-Ser/Thr-Thr residues are present and the oxidative cleavage at C-terminal Tyr/Trp sites generating des amides. The oxidative methodology presented here is mild, simple, and practical and proceeds with chiral retention. The insensitivity of a large number of amino acid residues, such as Gly, Ala, Leu, Asn, Gln, Asp, Glu, Pro, Arg, Phe, Lys, Val, and Aib, and N-protecting groups, such as Boc, Z, and Bz, toward Ru(VIII) under the experimental conditions should make this methodology practical and useful. Sulfur-containing amino acids Cys and Met get oxidized to sulfones in the products.
• RANGANATHAN, DARSHAN;SAINI, SUJATA, J. AMER. CHEM. SOC., 113,(1991) N, C. 1042-1044
  作者：RANGANATHAN, DARSHAN、SAINI, SUJATA

  DOI：——

  日期：——
• Konopinska,D., Polish Journal of Chemistry, 1978, vol. 52, p. 953 - 957
  作者：Konopinska,D.

  DOI：——

  日期：——