Z-Gly-D-Ala-OMe | 24955-56-4

• 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-Gly-D-Ala-OMe
• 英文别名: methyl (2R)-2-[[2-(phenylmethoxycarbonylamino)acetyl]amino]propanoate
• CAS: 24955-56-4
• 化学式: C₁₄H₁₈N₂O₅
• 分子量: 294.307
• InChiKey: FRAUDHDTLOHHJY-SNVBAGLBSA-N

物化性质

• 沸点：
  495.4±35.0 °C(Predicted)
• 密度：
  1.209±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Z-Gly-D-Ala-OMe 在 氢气 作用下， 反应 1.5h， 生成 cyclo(-dehydrophenylalanyl-D-alanyl-)
  参考文献：
  名称：

  Facile synthesis of (2R, 3R)-phenylalanine-2,3-d2 and its application to conformational analysis of gramicidin S

  摘要：

  DOI：

  10.1016/s0040-4039(00)94522-2
• 作为产物：
  描述：

  N-苄氧羰基甘氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 吡啶 、 二氯甲烷 、 三乙胺 为溶剂， 反应 24.0h， 生成 Z-Gly-D-Ala-OMe
  参考文献：
  名称：

  Effenberger, Franz; Brodt, Werner, Chemische Berichte, 1985, vol. 118, # 2, p. 468 - 482

  摘要：

  DOI：

文献信息

• Papain catalysed peptide synthesis: control of amidase activity and the introduction of unusual amino acids
  作者：Carlos F. Barbas、Chi-Huey Wong

  DOI：10.1039/c39870000533

  日期：——

  Procedures for the papain catalysed synthesis of peptides containing D-amino acids and derivatives with control of the enzyme's amidase activity have been developed.

  已经开发了木瓜蛋白酶催化的合成含有D-氨基酸的肽和可控制该酶的酰胺酶活性的衍生物的方法。
• Facile Synthesis of (2<i>R</i>,3<i>R</i>)-Phenylalanine-2,3-<i>d</i>₂and NMR Study on Deuterated Gramicidin S
  作者：Kenjiro Tanimura、Tetsuo Kato、Michinori Waki、Sannamu Lee、Yasushi Kodera、Nobuo Izumiya

  DOI：10.1246/bcsj.57.2193

  日期：1984.8

  (2R,3R)-Phenylalanine-2,3-d2 (d-Phe*) was synthesized through catalytic reduction of cyclo(-(Z)-2,3-dehydrophenylalanyl-d-alanyl-) under an atmosphere of 2H2 and successive acid hydrolysis in the yield of 80% in high chiral induction. The d-Phe* thus obtained was used for synthesis of [d-Phe*4,4′] gramicidin S (GS*). The 1H NMR spectrum of GS* in DMSO-d6 showed a sharp singlet at 2.98 ppm for the (3S)-proton of d-Phe* residue. It has been proposed that among rotamers of d-Phe aromatic side chain in GS the one with κ1=180° is predominant. The present observation provides sound evidence for assignments of d-Phe β-protons based on the proposal.

  (2R,3R)-苯丙氨酸-2,3-d2 (d-Phe*)通过环(-(Z)-2,3-脱氢苯丙氨酰-d-丙氨酰-)在2H2气氛下催化还原和连续反应合成在高手性诱导下酸水解产率达80%。由此获得的d-Phe*用于合成[d-Phe*4,4']短杆菌肽S(GS*)。 DMSO-d6 中 GS* 的 1H NMR 谱显示 d-Phe* 残基的 (3S)-质子在 2.98 ppm 处有尖锐的单线态。有人提出，GS d-Phe 芳香族侧链的旋转异构体中，κ1=180° 的旋转异构体占主导地位。目前的观察结果为基于该提议的 d-Phe β-质子分配提供了可靠的证据。
• Synthesis, antibacterial activities, and pharmacological properties of enantiomers of temafloxacin hydrochloride
  作者：Daniel T. W. Chu、Carl W. Nordeen、Dwight J. Hardy、Robert N. Swanson、William J. Giardina、Andre G. Pernet、Jacob J. Plattner

  DOI：10.1021/jm00105a025

  日期：1991.1

  Temafloxacin hydrochloride [(+/-)-7-(3-methylpiperazin-1-yl)-6-fluro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride] is a potent member of the 4-pyridone-3-carboxylic acid class of antibacterial agents and is currently under clinical development as a broad-spectrum antimicrobial agent. It is a racemate having a chiral center at the C3 of the 7-piperazin-1-yl group. The two enantiomers were synthesized and tested for their antibacterial activities. Although no difference in in vitro antibacterial activities was observed, a minor difference in in vivo antibacterial activities was observed. However, they both exhibited similar pharmacological profiles.
• Kaminski; Kolesinska; Markowicz, Polish Journal of Chemistry, 1999, vol. 73, # 12, p. 1965 - 1968
  作者：Kaminski、Kolesinska、Markowicz、Pokrzeptowicz

  DOI：——

  日期：——
• Kruszynski,M.; Kupryszewski,G., Roczniki Chemii, 1976, vol. 50, p. 1099 - 1115
  作者：Kruszynski,M.、Kupryszewski,G.

  DOI：——

  日期：——