Fmoc-Phe(p-CHO)-OMe | 945245-50-1

• 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: Fmoc-Phe(p-CHO)-OMe
• 英文别名: N-(fluorenyl-9-methoxycarbonyl)-L-p-formyl-phenylalanine methyl ester
• CAS: 945245-50-1
• 化学式: C₂₆H₂₃NO₅
• 分子量: 429.472
• InChiKey: ODXULTKJPJKOFT-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.12
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Phe(p-CHO)-OMe 在 sodium tetrahydroborate 、 N-溴代丁二酰亚胺(NBS) 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 0.67h， 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：

  N-[芴甲氧羰基]-L-酪氨酸甲酯 在 palladium diacetate 吡啶 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.84h， 生成 Fmoc-Phe(p-CHO)-OMe
  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

文献信息

• Synthesis of <i>meso</i>-tetraarylporphyrins possessing amino and carboxy groups and their peptides
  作者：Hitoshi Tamiaki、Takaaki Kozawa、Rika Kitamoto、Michio Kunieda

  DOI：10.1142/s1088424610002197

  日期：2010.5

  with L-phenylalanine (H-Phe-OH) directly at the unsubstituted meso-position of the former and the p-position of phenyl group of the latter to afford chiral porphyrin-amino acid conjugate H-Phe(p-P)-OH. The N-(9-fluorenyl)-methyloxycarbonyl compound, Fmoc-Phe(p-P)-OH, was synthesized without any loss of enantiomeric purity (based on chiral HPLC analysis) from commercially available L-tyrosine and was

  meso-Tris(3,5-di-tert-butylphenyl)porphyrin (P-H) 与 L-苯丙氨酸 (H-Phe-OH) 直接在前者的未取代的中间位和苯基的对位键合后者的组提供手性卟啉-氨基酸缀合物H-Phe(pP)-OH。N-(9-芴基)-甲氧羰基化合物 Fmoc-Phe(pP)-OH 是从市售 L-酪氨酸合成的，对映体纯度没有任何损失（基于手性 HPLC 分析），可用于制备肽在液相和固相中。报道了具有多氨基酸部分的其他内消旋四芳基卟啉，以及容易制备的非手性卟啉-氨基酸及其二肽基卟啉二联体。