N-maleyl-L-phenylalanine | 57079-18-2

• 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: N-maleyl-L-phenylalanine
• 英文别名: Mal-Phe-OH；(Z)-N-(3-Carboxy-1-oxo-2-propenyl)-L-phenylalanine；(Z)-4-[[(1S)-1-carboxy-2-phenylethyl]amino]-4-oxobut-2-enoic acid
• CAS: 57079-18-2
• 化学式: C₁₃H₁₃NO₅
• 分子量: 263.25
• InChiKey: OQGKOQBYSJCHHV-GFVADAIESA-N

物化性质

• 熔点：
  141-143 °C(Solv: cyclohexane (110-82-7); ethyl ether (60-29-7))
• 沸点：
  580.7±50.0 °C(Predicted)
• 密度：
  1.357±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-maleyl-L-phenylalanine 在 六甲基二硅氮烷 、 苯磺酸 、 zinc(II) chloride 作用下， 以 甲苯 、 苯 为溶剂， 反应 18.0h， 生成 N,N-maleoyl-L-Phe-OMe
  参考文献：
  名称：

  Bodtke; Otto, Hans-Hartwig, Pharmazie, 2005, vol. 60, # 11, p. 803 - 813

  摘要：

  DOI：
• 作为产物：
  描述：

  马来酰苯丙氨酸甲酯 在 chymotrypsin 作用下， 以 水 为溶剂， 生成 N-maleyl-L-phenylalanine
  参考文献：
  名称：

  Schellenberger, Volker; Schellenberger, Ute; Jakubke, Hans-Dieter, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11B, p. 2884 - 2889

  摘要：

  DOI：

文献信息

• Process for the conversion of maleic acid derivatives to their
  申请人：The NutraSweet Company

  公开号：USH0000645H1

  公开（公告）日：1989-06-06

  A process for the isomerization of maleic acid, its monoesters and monoamides in the presence of thiourea in anhydrous conditions at elevated temperature to the corresponding fumaryl forms yields intermediates which are useful in the synthetic pathways of aspartame and other useful polypeptides.

  在无水条件下，在高温下存在硫脲的情况下对马来酸及其单酯和单酰胺进行异构化的过程，可以得到相应的富马酸形式的中间体，这些中间体在阿斯巴甜和其他有用的多肽的合成途径中是有用的。
• Schellenberger, Volker; Schellenberger, Ute; Jakubke, Hans-Dieter, Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11B, p. 2884 - 2889
  作者：Schellenberger, Volker、Schellenberger, Ute、Jakubke, Hans-Dieter

  DOI：——

  日期：——
• Alkylating derivatives of amino acids and peptides. Synthesis of N-maleoylamino acids, [1-(N-maleoylglycyl)cysteinyl]oxytocin, and [1-(N-maleoyl-11-aminoundecanoyl)cysteinyl]oxytocin. Effects on vasopressin-stimulated water loss from isolated toad bladder
  作者：Daniel H. Rich、Paul D. Gesellchen、Alex Tong、Al Cheung、Carl K. Buckner

  DOI：10.1021/jm00244a011

  日期：1975.10

  A method for the preparation of N-maleoylamino acids and esters is reported. These compounds were shown to inhibit both the oxytocin-induced smooth muscle contraction in the isolated rat uterus and the vasopressin-induced water loss from the isolated toad bladder. The inhibitory ability of the maleimides in the toad bladder assay was found to be related to their corresponding partition coefficients by the equation: log 1/C = -0.055 (log P) 2 + 0.227 log P + 3.96. N-Maleoylamino acids can be coupled to peptides to form alkylating reagents which react rapidly with sulfhydryl groups. The synthesis of [1-(N-maleoylglycyl)cysteinyl]oxytocin (3) and [1=(N-maleoyl-11-aminoundecanoyl)cysteinyl]oxytocin (4) as potential affinity labeling reagents is described. These oxytocin analogs were shown to readily react with sulfhydryl-containing compounds; however, neither 3 nor 4 was seen to inhibit in the rat uterus assay at concentrations up to 3 times 10(-5)M. When tested on the mucosal and serosal surfaces of the toad bladder, assay inhibition was seen only on the mucosal surface. These results are discussed with respect to the possible existence of sulfhydryl groups at neurohypophyseal receptors.
• JPS63270652A
  申请人：——

  公开号：JPS63270652A

  公开（公告）日：1988-11-08
• USH645H
  申请人：——

  公开号：USH645H

  公开（公告）日：1989-06-06