Z-Thr-Phe-OMe | 19649-01-5

• 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-Phe-OMe
• 英文别名: N-Benzyloxycarbonyl-Ls-threonyl-L-phenylalanin-methylester；Benzyloxycarbonyl-threonyl-phenylalanin-methylester (L)；methyl (2S)-2-[[(2S,3R)-3-hydroxy-2-(phenylmethoxycarbonylamino)butanoyl]amino]-3-phenylpropanoate
• CAS: 19649-01-5
• 化学式: C₂₂H₂₆N₂O₆
• 分子量: 414.458
• InChiKey: FOULQMVLUUSLJT-MNEFBYGVSA-N

物化性质

• 熔点：
  105-107 °C(Solv: benzene (71-43-2); ligroine (8032-32-4))
• 沸点：
  649.9±55.0 °C(Predicted)
• 密度：
  1.235±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 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-Phe-OMe 在 盐酸 、 亚硝酸特丁酯 、 氢气 、 一水合肼 、 三乙胺 作用下， 以 甲醇 、 溶剂黄146 、 乙酸乙酯 为溶剂， 反应 48.33h， 生成 Boc-Lys(Z)-Thr-Phe-Thr-Ser-NHNH2
  参考文献：
  名称：

  Giori; Veronese; Vicentini, European Journal of Medicinal Chemistry, 1982, vol. 17, # 6, p. 515 - 520

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl (2S,3R)-2-(benzyloxycarbonylamino)-3-hydroxybutyrate 在 一水合肼 作用下， 以 甲醇 为溶剂， 反应 2.0h， 生成 Z-Thr-Phe-OMe
  参考文献：
  名称：

  Schroeder,E.; Gibian,H., Justus Liebigs Annalen der Chemie, 1962, vol. 656, p. 190 - 204

  摘要：

  DOI：

文献信息

• A new convenient approach to peptide synthesis using a diselenide and a phosphine
  作者：Usha Singh、Sunil K. Ghosh、Mohindra S. Chadha、Vasant R. Mamdapur

  DOI：10.1016/0040-4039(91)80869-8

  日期：1991.1

  A new and highly efficient method based on a redox reaction using diphenyl diselenide and tributylphosphine for the general synthesis of peptides is described. The side reaction due to selenophenol formation is overcome by using chalcone as a scavenger or by selective oxidation to diselenide.

  描述了一种基于氧化还原反应的新型高效方法，该方法使用二苯二硒化物和三丁基膦进行肽的一般合成。通过使用查尔酮作为清除剂或通过选择性氧化成二硒化物，可以克服由于硒酚形成而引起的副反应。
• Amino Acids and Peptides. XI. Phosphorus in Organic Synthesis. VI. Application of Diphenyl Phosphorazidate to the Synthesis of Peptides containing Various Functions
  作者：TAKAYUKI SHIOIRI、SHUNICHI YAMADA

  DOI：10.1248/cpb.22.859

  日期：——

  Application of diphenyl phosphorazidate (DPPA) to the synthesis of peptides revealed that the DPPA method is quite general because it can be applied to the formation of peptides containing various functional groups. No difficulties were encountered when the side chains of serine, threonine, valine, glutamine, asparagine, methionine, histidine, tryptophan, and pyroglutamic acid were present in the carboxyl component. Arginine and cysteine showed no trouble when their side chain functions were protected with the nitro and benzyl groups, respectively. Serine, tyrosine, and histidine could be used as the amino component without any protection of the side chains. Fragment coupling of N-benzyloxycarbonylleucylleucine with valylphenylalanine methyl ester hydrochloride by DPPA showed that no racemization occurred.

  将磷酸二苯酯（DPPA）应用于多肽合成的结果表明，DPPA 方法具有很强的通用性，因为它可以用于合成含有各种官能团的多肽。当羧基成分中含有丝氨酸、苏氨酸、缬氨酸、谷氨酰胺、天冬酰胺、蛋氨酸、组氨酸、色氨酸和焦谷氨酸的侧链时，没有遇到任何困难。当精氨酸和半胱氨酸的侧链功能分别受到硝基和苄基的保护时，不会出现问题。丝氨酸、酪氨酸和组氨酸可用作氨基成分，无需对侧链进行任何保护。用 DPPA 将 N-苄氧羰基亮氨酸与戊基苯丙氨酸甲酯盐酸盐进行片段偶联，结果表明没有发生外消旋现象。
• 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
• 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.
• Miroshnikov,A.I. et al., Journal of general chemistry of the USSR, 1970, vol. 40, # 2, p. 395 - 407
  作者：Miroshnikov,A.I. et al.

  DOI：——

  日期：——