Z-Ser-Phe-OMe | 40290-58-2

• 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: Z-Ser-Phe-OMe
• 英文别名: methyl (2S)-2-[[(2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]-3-phenylpropanoate
• CAS: 40290-58-2
• 化学式: C₂₁H₂₄N₂O₆
• 分子量: 400.431
• InChiKey: VTWVQIIQSVGKKO-ROUUACIJSA-N

物化性质

• 熔点：
  102-104 °C
• 沸点：
  649.6±55.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  29
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 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-Ser-Phe-OMe 在 lithium nitrate 、 sodium carbonate 、 三氟乙酸酐 作用下， 以 乙腈 为溶剂， 以70%的产率得到(S)-2-((S)-2-Benzyloxycarbonylamino-3-nitrooxy-propionylamino)-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  使用LiNO 3 /（CF 3 CO）2 O从醇制备硝酸酯的简便方法

  摘要：

  在用LiNO 3和三氟乙酸酐的乙腈溶液处理后，小肽，单糖和类固醇中的醇（12个实例）可以方便地转化为它们相应的硝酸酯。有人提出将原位形成的混合酸酐（CF 3 COONO 2）用作反应性硝化试剂。

  DOI：

  10.1016/j.tetlet.2005.07.065
• 作为产物：
  描述：

  L-苯丙氨酸甲酯盐酸盐 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-Ser-Phe-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

• Transformation of C-terminal serine and threonine extended precursors into C-terminal .alpha.-amidated peptides: a possible chemical model for the .alpha.-amidating action of pituitary enzymes
  作者：Darshan Ranganathan、Sujata Saini

  DOI：10.1021/ja00003a048

  日期：1991.1

  The chemical model presented here affords a mild and practical methodology for the preparation of C-terminal amides from C-terminal Ser/Thr extended precursors. Further, the oxalamides derived from N-terminal and nonterminal Ser/Thr peptides constitute an entirely novel class of peptide analogues possessing extended planar bis-peptide regions, the study of whose conformational and reactivity profile

  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
• Hydroxy-directed peptide bond formation from α-amino acid-derived inert esters enabled by boronic acid catalysis
  作者：Naoya Takahashi、Airi Takahashi、Naoyuki Shimada

  DOI：10.1039/d3cc04856j

  日期：——

  acid-catalyzed peptide bond formation from α-amino acid methyl esters is described. The catalysis showed high chemoselectivity for β-hydroxy-α-amino esters, affording the peptides in high to excellent yields with high functional group tolerance. This hydroxy-directed peptide bond formation could be applicable to oligopeptide syntheses. This is the first successful example of organoboron-catalyzed peptide bond

  描述了硼酸催化 α-氨基酸甲酯形成肽键。该催化对 β-羟基-α-氨基酯表现出高化学选择性，使肽具有高至优异的产率和高官能团耐受性。这种羟基定向的肽键形成可适用于寡肽合成。这是有机硼催化α-氨基酸衍生的惰性酯形成肽键的第一个成功例子。
• 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：——
• A convenient and simple procedure for the preparation of nitrate esters from alcohols employing LiNO3/(CF3CO)2O
  作者：Adina Gavrila、Lisbeth Andersen、Troels Skrydstrup

  DOI：10.1016/j.tetlet.2005.07.065

  日期：2005.9

  Alcohols in small peptides, monosaccharides and steroids (12 examples) are conveniently transformed to their corresponding nitrate esters upon treatment with an acetonitrile solution of LiNO3 and trifluoroacetic anhydride. The in situ formed mixed anhydride (CF3COONO2) is proposed to be the reactive nitration reagent.

  在用LiNO 3和三氟乙酸酐的乙腈溶液处理后，小肽，单糖和类固醇中的醇（12个实例）可以方便地转化为它们相应的硝酸酯。有人提出将原位形成的混合酸酐（CF 3 COONO 2）用作反应性硝化试剂。