Fmoc-Ala-O-CH2PhOCH2CH2COOH | 864876-89-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Ala-O-CH2PhOCH2CH2COOH
• 英文别名: Fmoc-Ala-HMPBA；Fmoc-L-Ala-MPPA；3-[4-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]oxymethyl]phenoxy]propanoic acid
• CAS: 864876-89-1
• 化学式: C₂₈H₂₇NO₇
• 分子量: 489.525
• InChiKey: BPYABFPWXINFTE-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.51
• 重原子数：
  36.0
• 可旋转键数：
  10.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  111.16
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Fmoc-Ala-O-CH2PhOCH2CH2COOH 、 Fmoc-L-脯氨酸 、 Fmoc-L-苯丙氨酸 在 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成
  参考文献：
  名称：

  Synthesis of the All-l Cyclopentapeptides Versicoloritides A, B, and C

  摘要：

  Herein we describe the first synthesis of the all-L naturally occurring cyclopentapeptides versicoloritides A, B, and C. We found that the extent of oligomerization and epimerization upon head-to-tail cyclization of the linear pentapeptide precursors could be reduced to acceptable levels by modifying the reaction conditions.

  DOI：

  10.1055/s-0032-1316994

文献信息

• Synthesis of an Isotopically-labelled Antarctic Fish Antifreeze Glycoprotein Probe
  作者：Joanna M. Wojnar、Clive W. Evans、Arthur L. DeVries、Margaret A. Brimble

  DOI：10.1071/ch10464

  日期：——

  Antifreeze glycoproteins (AFGPs) are glycosylated polypeptides produced by Antarctic and Arctic fishes, which allow them to survive in seawater at sub-zero temperatures. An investigation into the postulated enteric uptake of AFGP synthesized in the exocrine pancreas of Antarctic fishes required a custom-prepared AFGP probe that incorporated seven isotopically-labelled Ala residues for detection by

  抗冻糖蛋白（AFGP）是南极和北极鱼类产生的糖基化多肽，可以使它们在低于零温度的海水中生存。对南极鱼类外分泌胰腺中合成的AFGP的假定肠摄取的调查，需要定制的AFGP探针，该探针结合了7个同位素标记的Ala残基，用于质谱检测。的AFGPs由重复的三个氨基酸单元（丙氨酸-丙氨酸-苏氨酸），其中，所述苏氨酸残基是糖基化与二糖的β- d -Gal-（1→3）-α- d -GalNAc。同位素标记的AFGP8（1）的合成，以及受保护的糖基化氨基酸构件2的优化合成，已报告。
• Synthesis and biological evaluation of the osteoblast proliferating cyclic peptides dianthins G and H
  作者：Harveen Kaur、Amanda M. Heapy、Renata Kowalczyk、Zaid Amso、Maureen Watson、Jillian Cornish、Margaret A. Brimble

  DOI：10.1016/j.tet.2014.04.035

  日期：2014.10

  The first synthesis and osteoblast proliferative activity of the naturally occurring cyclic peptides dianthins G and H is described. The greater potency of naturally occurring dianthin G over dianthin H at physiological concentrations mirrored the osteoblast proliferative activity observed for synthetic dianthins G and H. Six alanine-scan analogues of the more potent dianthin G were also synthesised and osteoblast assays revealed that four of the six residues can be further modified for improved activity. We also confirmed by variable temperature H-1 NMR spectroscopic analysis that the sets of major and minor signals observed for dianthins G and H in DMSO-d(6) are in fact due to cis-trans rotational isomers of the praline ring. (C) 2014 Elsevier Ltd. All rights reserved.
• Synthesis of the All-l Cyclopentapeptides Versicoloritides A, B, and C
  作者：Margaret Brimble、Harveen Kaur、Amanda Heapy

  DOI：10.1055/s-0032-1316994

  日期：——

  Herein we describe the first synthesis of the all-L naturally occurring cyclopentapeptides versicoloritides A, B, and C. We found that the extent of oligomerization and epimerization upon head-to-tail cyclization of the linear pentapeptide precursors could be reduced to acceptable levels by modifying the reaction conditions.