Z-(S)-Val-Cl | 87052-60-6

• 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-(S)-Val-Cl
• 英文别名: Z-(L)-Val-Cl；N-Cbz-L-valine acid chloride；N-Benzyloxycarbonyl-L-valinchlorid；N-benzyloxycarbonyl-L-valyl chloride；benzyl N-[(2S)-1-chloro-3-methyl-1-oxobutan-2-yl]carbamate
• CAS: 87052-60-6
• 化学式: C₁₃H₁₆ClNO₃
• 分子量: 269.728
• InChiKey: ZIFXIKJIMMTFBA-NSHDSACASA-N

物化性质

• 沸点：
  385.2±35.0 °C(Predicted)
• 密度：
  1.191±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  55.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Z-(S)-Val-Cl 在 钯 N-甲基吗啉 、 氢气 作用下， 以 二氯甲烷 为溶剂， 生成 (L-Valyl)-L-phenylalanyl-L-prolin-lactam
  参考文献：
  名称：

  Losse; Wehrstedt, Zeitschrift fur Chemie, 1981, vol. 21, # 4, p. 148 - 149

  摘要：

  DOI：
• 作为产物：
  描述：

  CBZ-L-缬氨酸 在 1-氯-N,N,2-三甲基丙烯胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.17h， 生成 Z-(S)-Val-Cl
  参考文献：
  名称：

  Amino Acids and Peptides; 67.¹Easy Preparation and Use of Benzyloxycarbonyl Derivatives of Amino Acid Chlorides and α-Hydroxycarboxylic Acid Chlorides

  摘要：

  N-苄氧羰基氨基酸氯化物和α-苄氧羰氧基羧酸氯化物可以通过将相应的羧酸与1-氯-N，N，2-三甲基-1-丙烯-1-胺反应而容易地制备。它们可以直接与O、N和C亲核试剂反应，生成肽、酮和酯。

  DOI：

  10.1055/s-1988-27612

文献信息

• One-pot synthesis of Weinreb amides employing 3,3-dichloro-1,2-diphenylcyclopropene (CPI-Cl) as a chlorinating agent
  作者：Shekharappa M、Roopesh Kumar L、Vommina V. Sureshbabu

  DOI：10.1080/00397911.2018.1531295

  日期：2019.3.19

  Abstract The synthesis of Nα-protected amino alkyl Weinreb amides starting from the corresponding α-amino acids as well as carboxylic acids has been delineated through the in situ generation of acid chlorides using CPI-Cl as a chlorinating agent. The protocol is simple; the reaction conditions employed were mild, and compatible with all the three commonly used urethane protecting groups namely, Boc

  摘要 通过使用 CPI-Cl 作为氯化剂原位生成酰氯，从相应的 α-氨基酸和羧酸开始合成 Nα-保护的氨基烷基 Weinreb 酰胺。协议很简单；所采用的反应条件温和，并与所有三种常用的氨基甲酸酯保护基团兼容，即 Boc、Cbz 和 Fmoc 基团。得到的 Weinreb 酰胺作为光学纯产品以良好的产率获得。图形概要
• Studies of Unusual Amino Acids and Their Peptides. XIII. The Chemistry of<i>N</i>-(Carboxy methyl) amino Acids. II. The Synthesis of Peptides Containing<i>N</i>-(Carboxymethyl) amino Acids
  作者：Toshifumi Miyazawa

  DOI：10.1246/bcsj.53.3661

  日期：1980.12

  Z–Cm-amino acid derivatives as the carboxyl components. On the other hand, a peptide using a Cm-amino acid diester as the amino component could not be prepared by the usual methods mentioned above. The desired compound was eventually obtained by the acid chloride method. A peptide containing a Cm-amino acid with the free imino group was also prepared by the condensation of a bromoacetylated amino acid ester

  研究了N-羧甲基(Cm-)氨基酸合成肽的基本问题。通过用于母体氨基酸的常规方法获得了几种游离Cm-氨基酸的N-保护衍生物及其单酯的N-苄氧羰基(Z)衍生物。在 Cm 氨基酸的任一羧基上形成肽键被证明可以通过常用方法实现，例如碳二亚胺、二环己基碳二亚胺-1-羟基苯并三唑或混合酸酐方法，如使用 Z-Cm 的示例所示-氨基酸衍生物作为羧基组分。另一方面，使用Cm-氨基酸二酯作为氨基组分的肽不能通过上述常用方法制备。最终通过酰氯法得到所需化合物。
• The Total Synthesis of Antrimycin D_v; II:¹Synthesis of Tetrahydropyridazinecarboxylic Acid and Its Incorporation into Peptides
  作者：Ulrich Schmidt、Bernd Riedl

  DOI：10.1055/s-1993-25947

  日期：——

  Appropriately protected di- and tripeptides containing (R, S)-tetra -hydropyridazine-3-carboxylic acids were synthesized via protected γ-formyl-α-hydrazinobutyric acids. The latter compounds are obtained from acetals of either ethyl γ-formylbutyrate or ethyl γ-formyl-α-oxobutyrate.

  通过受保护的δ-α-肼丁酸合成了含有(R, S)-四氢哒嗪-3-羧酸的经适当保护的二肽和三肽。后一种化合物是从δ-甲酰基丁酸乙酯或δ-甲酰基-δ-氧代丁酸乙酯的缩醛中获得的。
• 一种水溶性氟苯尼考氨基酸盐的制备方法
  申请人：中国农业大学

  公开号：CN111393341A

  公开（公告）日：2020-07-10

  本发明公开了一种水溶性氟苯尼考氨基酸酯盐的制备方法，所述方法，以氟苯尼考和N‑Cbz‑氨基酸为起始原料，经过酰氯化、酯化、脱保护和酸化成盐反应，得到水溶性的氟苯尼考氨基酸酯盐。本发明中原料商业可得、成本低，反应过程中各单元反应条件温和可控，收率高，得到的氟苯尼考氨基酸酯盐纯度高、水溶性好，适用于水溶性氟苯尼考氨基酸酯盐的大规模生产应用。
• Amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole as acid-stable prodrugs of potential inhibitors of H+K+ ATPase
  作者：K Hirai、H Koike、T Ishiba、S Ueda、I Makino、H Yamada、T Ichihashi、Y Mizushima、M Ishikawa、Y Ishihara、Y Hara、H Hirose、N Shima、M Doteuchi

  DOI：10.1016/0223-5234(91)90024-h

  日期：1991.3

  A series of amino acid amides of 2-[(2-aminobenzyl)sulfinyl]benzimidazole were prepared and found to possess gastric antisecretory activity on oral administration. (Glycylaminobenzyl)sulfinyl compound 23a, stable in artificial gastric juice (pH 1.2), was given orally to dogs. It was absorbed efficiently and converted into aniline derivative 7a which showed a very high plasma concentration. Compound 23a was hydrolyzed by the action of aminopeptidase present in plasma or the brush border fraction of the small intestine to release the terminal glycine. omicron-Aniline derivatives showed good activity in in vitro H+/K+-ATPase inhibition as well as in the inhibition of histamine stimulated acid secretion in isolated bullfrog gastric mucosa. Although these omicron-aniline derivatives showed no or weak gastric antisecretory activity in rat by id administration, they were active when administered ip. Therefore, these amino acid amides were considered to be acid stable prodrugs of proton pump inhibiting omicron-aniline derivatives. The mechanism of H+/K+-ATPase inhibition of 7a was also examined.