N-Acetyl (4-hydroxymethyl)-DL-phenylalanine | 15742-86-6

• 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: N-Acetyl (4-hydroxymethyl)-DL-phenylalanine
• 英文别名: N-acetyl-(p-hydroxymethyl)phenylalanine；N-Acetyl-DL-p-hydroxymethylphenylalanin；2-Acetamido-3-[4-(hydroxymethyl)phenyl]propanoic acid
• CAS: 15742-86-6
• 化学式: C₁₂H₁₅NO₄
• 分子量: 237.255
• InChiKey: XNHWYBHHSPUPDE-UHFFFAOYSA-N

物化性质

• 沸点：
  535.8±50.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  86.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-Acetyl (4-hydroxymethyl)-DL-phenylalanine 在 氢氧化钾 、 N-溴代丁二酰亚胺(NBS) 、 氯化亚砜 、 水 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 144.0h， 生成 N-(fluorenyl-9-methoxycarbonyl)-L-(p-bromomethyl)phenylalanine methyl ester
  参考文献：
  名称：

  (p-Sulfomethyl)phenylalanine as a mimic of O-sulfatyl-tyrosine in synthetic partial sequences of P-Selectin glycoprotein ligand 1 (PSGL-1)

  摘要：

  Fmoc-L-(p-sulfomethyl)phenylalanine, a bioisosteric mimic of acid-sensitive O-sulfatyl tyrosine, was synthesized from L-tyrosine according to a novel route. Partial sequences of the recognition site of P-Selectin glycoprotein ligand 1 (PSGL-1), which contain (sulfomethyl) phenylalanine were synthesized on solid-phase. By fragment condensation, a sialyl Lewis(x) peptide conjugate containing a (sulfomethyl)phenylalanine mimic of O-sulfatyl tyrosine was prepared without destruction of the acid-sensitive fucoside bond within the saccharide side chain. Compounds of this type are of interest as sufficiently acid-stable potential inhibitors of P-Selectin in inflammatory processes. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.03.028
• 作为产物：
  描述：

  对甲基苯甲酸甲酯 在 盐酸 aluminium hydride 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 sodium hydride 、 sodium carbonate 作用下， 以 四氯化碳 、 乙醚 、 水 、 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 29.0h， 生成 N-Acetyl (4-hydroxymethyl)-DL-phenylalanine
  参考文献：
  名称：

  Synthesis of 4-phosphono- and of 4-(phosphonomethyl)-dl-phenylalanine, two analogues of O-phosphotyrosine

  摘要：

  DOI：

  10.1016/s0040-4020(01)90076-6

文献信息

• Synthesis of novel chiral amino acids possessing a porphyrin moiety
  作者：Hitoshi Tamiaki、Motoki Onishi

  DOI：10.1016/s0957-4166(99)00101-9

  日期：1999.3

  Phenylalanine derivatives bearing a porphyrin moiety at the para-position were prepared in an enantiomerically pure form. The synthetic nonnatural aromatic amino acid reacted with amines and acids to give novel functionalized peptides without loss of the enantiomeric purity.

  以对映体纯的形式制备在对位带有卟啉部分的苯丙氨酸衍生物。合成的非天然芳族氨基酸与胺和酸反应，得到新的功能化肽，而不会损失对映体纯度。
• PROCESS FOR PRODUCTION OF OPTICALLY ACTIVE HYDROXYMETHYL-SUBSTITUTED PHENYLALANINE
  申请人：NAKAZAWA Masakazu

  公开号：US20080241896A1

  公开（公告）日：2008-10-02

  The present invention provides a production method of optically active hydroxymethyl-substituted phenylalanine, which includes reducing cyano-substituted benzylidene hydantoin (1) to give aminomethyl-substituted benzyl hydantoin (2) or a salt thereof, converting an amino group of the aminomethyl-substituted benzyl hydantoin (2) or a salt thereof to a hydroxyl group to give hydroxymethyl-substituted benzyl hydantoin (3), treating the hydroxymethyl-substituted benzyl hydantoin (3) with an enzyme to give D-hydroxymethyl-substituted phenylalanine (4 a ) or a salt thereof, or L-hydroxymethyl-substituted phenylalanine (4 b ) or a salt thereof. According to the present invention, a production method capable of conveniently producing optically active hydroxymethyl-substituted phenylalanine on an industrial scale can be provided.

  本发明提供了一种光学活性的羟甲基取代苯丙氨酸的生产方法，包括将氰基取代苯并咪唑酮（1）还原为氨基甲基取代苯并咪唑酮（2）或其盐，将氨基甲基取代苯并咪唑酮（2）或其盐的氨基转化为羟基，得到羟甲基取代苯并咪唑酮（3），用酶处理羟甲基取代苯并咪唑酮（3）得到D-羟甲基取代苯丙氨酸（4a）或其盐，或L-羟甲基取代苯丙氨酸（4b）或其盐。根据本发明，可以提供一种能够方便地在工业规模下生产光学活性羟甲基取代苯丙氨酸的生产方法。
• α-Dicarbonyls as “non-charged” arginine-directed affinity labels. Novel synthetic routes to α-dicarbonyl analogs of the PP60c-src SH2 domain-targeted phosphopeptide Ac-Tyr(OPO3H2)-Glu-Glu-Ile-Glu
  作者：Mukund M. Mehrotra、Daniel D. Sternbach、Marc Rodriguez、Paul Charifson、Judd Berman

  DOI：10.1016/0960-894x(96)00349-6

  日期：1996.8

  The phosphopeptide 1 is a potent inhibitor of pp60(c-src) SH2 domain mediated phosphoprotein interactions (IC50 less than or equal to 0.5 mu M), hut lacks cell permeability. The syntheses of its less charged analogs 2 and 3 are described, in which the arginine-binding phosphate group has been substituted with uncharged alpha-dicarbonyl moieties. The chemistry described here may be of general use for the synthesis of other alpha-dicarbonyl compounds. Copyright (C) 1996 Elsevier Science Ltd
• (p-Sulfomethyl)phenylalanine as a mimic of O-sulfatyl-tyrosine in synthetic partial sequences of P-Selectin glycoprotein ligand 1 (PSGL-1)
  作者：Holger Herzner、Horst Kunz

  DOI：10.1016/j.tet.2007.03.028

  日期：2007.7

  Fmoc-L-(p-sulfomethyl)phenylalanine, a bioisosteric mimic of acid-sensitive O-sulfatyl tyrosine, was synthesized from L-tyrosine according to a novel route. Partial sequences of the recognition site of P-Selectin glycoprotein ligand 1 (PSGL-1), which contain (sulfomethyl) phenylalanine were synthesized on solid-phase. By fragment condensation, a sialyl Lewis(x) peptide conjugate containing a (sulfomethyl)phenylalanine mimic of O-sulfatyl tyrosine was prepared without destruction of the acid-sensitive fucoside bond within the saccharide side chain. Compounds of this type are of interest as sufficiently acid-stable potential inhibitors of P-Selectin in inflammatory processes. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of 4-phosphono- and of 4-(phosphonomethyl)-dl-phenylalanine, two analogues of O-phosphotyrosine
  作者：Mireille Bayle-Lacoste、Jean Moulines、Noël Collignon、Abdelkader Boumekouez、Eliane de Tinguy-Moreaud、Eugéne Neuzil

  DOI：10.1016/s0040-4020(01)90076-6

  日期：1990.1