Z-Ser-Ala-OMe | 38428-20-5

• 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-Ser-Ala-OMe
• 英文别名: L-Alanine, N-[N-[(phenylmethoxy)carbonyl]-L-seryl]-, methyl ester；methyl (2S)-2-[[(2S)-3-hydroxy-2-(phenylmethoxycarbonylamino)propanoyl]amino]propanoate
• CAS: 38428-20-5
• 化学式: C₁₅H₂₀N₂O₆
• 分子量: 324.334
• InChiKey: QWGCABODXPAQFR-JQWIXIFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  23
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 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-Ala-OMe 在 sodium hydroxide 作用下， 生成 N-Benzyloxycarbonyl-L-seryl-L-alanin
  参考文献：
  名称：

  Fruton, Journal of Biological Chemistry, 1942, vol. 146, p. 463,469

  摘要：

  DOI：
• 作为产物：
  描述：

  N-苄氧羰基-L-丝氨酸 、 L-丙氨酸甲酯盐酸盐 在 碳酸氢钠 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 以72%的产率得到Z-Ser-Ala-OMe
  参考文献：
  名称：

  Impact of Dehydroamino Acids on the Structure and Stability of Incipient 3₁₀-Helical Peptides

  摘要：

  A comparative study of the impact of small, medium-sized, and bulky alpha,beta-dehydroamino acids (Delta AAs) on the structure and stability of Balarams incipient 3(10)-helical peptide (1) is reported. Replacement of the N-terminal Aib residue of 1 with a Delta AA afforded peptides 2a-c that maintained the 3(10)-helical shape of 1. In contrast, installation of a Delta AA in place of Aib-3 yielded peptides 3a-c that preferred a beta-sheet-like conformation. The impact of the Delta AA on peptide structure was independent of size, with small (Delta Ala), medium-sized (Z-Delta Abu), and bulky (Delta Val) Delta AAs exerting similar effects. The proteolytic stabilities of 1 and its analogs were determined by incubation with Pronase. Z-Delta Abu and Delta Val increased the resistance of peptides to proteolysis when incorporated at the 3-position and had negligible impact on stability when placed at the 1-position, whereas Delta Ala-containing peptides degraded rapidly regardless of position. Exposure of peptides 2a-c and 3a-c to the reactive thiol cysteamine revealed that Delta Ala-containing peptides underwent conjugate addition at room temperature, while Z-Delta Abu- and Delta Val-containing peptides were inert even at elevated temperatures. These results suggest that both bulky and more accessible medium-sized Delta AAs should be valuable tools for bestowing rigidity and proteolytic stability on bioactive peptides.

  DOI：

  10.1021/acs.joc.9b02747

文献信息

• Development of Hydrophilic Polyacrylamide Gel-Based Condensing Reagents Comprised of Chlorotriazine
  作者：Kohei Yamada、Shota Hirozawa、Junqing Xia、Munetaka Kunishima

  DOI：10.1248/cpb.c20-00074

  日期：2020.6.1

  PAG-Trz-Cl, have been developed. PAG-Trz-Cls were synthesized using a chlorotriazine with an acrylamide moiety, acrylamide, and N,N'-methylenebisacrylamide via both precipitation and solution polymerization. Because PAG-Trz-Cls adequately swell in aqueous media, the amidation between polar carboxylic acids and amines afforded the corresponding amides in good yields.

  已经开发了基于亲水性聚丙烯酰胺凝胶的三嗪型缩合剂PAG-Trz-Cl。使用具有丙烯酰胺部分，丙烯酰胺和N，N'-亚甲基双丙烯酰胺的氯三嗪通过沉淀和溶液聚合合成PAG-Trz-Cls。因为PAG-Trz-Cls在水性介质中充分溶胀，所以极性羧酸和胺之间的酰胺化反应以高收率提供了相应的酰胺。
• Amino acids and peptides. XVII. Synthesis of a tridecapeptide corresponding to the sequence 165-177 of T-kininogen (tryptic peptide) containing Gln-Val-Val-Ala-Gly sequence and the relationship between structure and effect on thiol proteinase.
  作者：NAOKI TENO、SATOSHI TSUBOI、YOSHIO OKADA、NORIO ITOH、HIROSHI OKAMOTO

  DOI：10.1248/cpb.35.3853

  日期：——

  The tridecapeptide corresponding to the sequence 165-177 of T-kininogen (tryptic peptide) (I) containing Gln-Val-Val-Ala-Gly sequence was synthesized by a conventional solution method and its effect on thiol proteinase was examined. Although Z-Gln-Val-Val-Ala-Gly-OMe showed inhibitory activity towards papain and protective activity against T-kininogen-induced inhibition of papain, the tryptic peptide obtained did not exhibit any effect on thiol proteinase. In order to study the relationship between structure and effect on thiol proteinase, several compounds (II-VI) modified with various groups at the N-terminus of the Gln-Val-Val-Ala-Gly sequence were synthesized. Peptides V and VI, which have an aromatic ring at the N-terminus, exhibited weak inhibitory and significant protective activities. A small peptide such as Gln-Val-Val-Ala-Gly might be better able to approach papain than the tryptic peptide (I), and the aromatic ring associated with Gln-Val-Val-Ala-Gly at the N-terminus apparently strengthened the binding ability of the peptide to papain.

  与T-激肽原（胰蛋白酶肽）序列165-177对应的三肽（I），含有Gln-Val-Val-Ala-Gly序列，通过传统溶液法合成，并对其对巯基蛋白酶的作用进行了研究。尽管Z-Gln-Val-Val-Ala-Gly-OMe对木瓜蛋白酶表现出抑制活性，并能保护木瓜蛋白酶免受T-激肽原诱导的抑制，但所获得的胰蛋白酶肽对巯基蛋白酶没有任何作用。为了研究结构与对巯基蛋白酶作用之间的关系，合成了几种在Gln-Val-Val-Ala-Gly序列的N-末端修改了不同基团的化合物（II-VI）。具有芳香环的肽V和VI表现出弱抑制和显著保护活性。像Gln-Val-Val-Ala-Gly这样的小肽可能比肽（I）更容易接近木瓜蛋白酶，而Gln-Val-Val-Ala-Gly N-末端的芳香环显然增强了肽与木瓜蛋白酶的结合能力。
• Selective Cleavage of Serine Peptides
  作者：Takeo Kaneko、Ikuko Takeuchi、Toshishige Inui

  DOI：10.1246/bcsj.41.974

  日期：1968.4

  N-benzyloxycarbonyl-L-alanyl-L-serine methyl ester (I) with phosgene afforded the corresponding O-chlorocarbonyl derivative (II), which was then cyclized to methyl L-3-(N-benzyloxycarbonyl-L-alanyl)-2-oxo-oxazolidine-4-carboxylate (III) accompanied with N-benzyloxycarbonyl-L-alanyl-3-chloro-L-alanine methyl ester (IV) by refluxing in xylene. By the mild alkaline hydrolysis of III, N-benzyloxycarbonyl-L-alanine

  N-苄氧羰基-L-丙氨酰-L-丝氨酸甲酯(I)用光气处理得到相应的O-氯羰基衍生物(II)，然后将其环化为甲基L-3-(N-苄氧羰基-L-丙氨酰)-2-氧代-恶唑烷-4-羧酸酯 (III) 与 N-苄氧羰基-L-丙氨酰-3-氯-L-丙氨酸甲酯 (IV) 在二甲苯中回流。通过 III 的温和碱性水解，N-苄氧羰基-L-丙氨酸和 L-2-氧代-恶唑烷-4-羧酸 (V) 由于肽键的选择性裂解而分离，其中氨基丝氨酸残基参与了。这种方法也适用于其他三种丝氨酸肽；得到了同样的结果。
• 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
• 2-Isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline as a coupling reagent in peptide synthesis
  作者：Yoshiaki Kiso、Haruaki Yajima

  DOI：10.1039/c39720000942

  日期：——

  2-Isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline and two analgous compounds have been used as coupling reagent for peptide synthesis.

  2-异丁氧基-1-异丁氧基羰基-1,2-二氢喹啉和两种肛门化合物已被用作肽合成的偶联剂。