Fmoc-Gly-HMPP | 130914-04-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: Fmoc-Gly-HMPP
• 英文别名: Fmoc-Gly-MPPA；3-[4-[[2-(9H-fluoren-9-ylmethoxycarbonylamino)acetyl]oxymethyl]phenoxy]propanoic acid
• CAS: 130914-04-4
• 化学式: C₂₇H₂₅NO₇
• 分子量: 475.498
• InChiKey: WWMUULLYECHIJT-UHFFFAOYSA-N

物化性质

• 沸点：
  681.7±50.0 °C(Predicted)
• 密度：
  1.307±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Fmoc-Gly-HMPP 、 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 H-Phe-Pro-Phe-Pro-Gly-OH
  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 and in vitro bone cell activity of analogues of the cyclohexapeptide dianthin G
  作者：Zaid Amso、Renata Kowalczyk、Young-Eun Park、Maureen Watson、Jian-ming Lin、David S. Musson、Jillian Cornish、Margaret A. Brimble

  DOI：10.1039/c6ob00983b

  日期：——

  Dianthin G and its dicarba analogue were both shown to increase the number of human osteoblasts without affecting bone resorption.

  Dianthin G及其二碳模拟物均显示能增加人类成骨细胞的数量，而不影响骨吸收。
• Synthesis and incorporation of an advanced lipid peroxidation end-product building block into collagen mimetic peptides
  作者：Iman Kavianinia、Sung-Hyun Yang、Harveen Kaur、Paul W. R. Harris、Renwick C. J. Dobson、Antony J. Fairbanks、Margaret A. Brimble

  DOI：10.1039/c7cc05025a

  日期：——

  their potential therapeutic value, there are no suitably protected ALE building blocks reported in the literature to enable their site-specific incorporation into synthetic peptides. The synthesis of an Fmoc-protected ALE building block, Nϵ-(3-methylpyridinium)lysine (MP-lysine) and its incorporation into collagen model peptides is reported.

  晚期脂质过氧化终产物（ALE）会随着衰老和氧化应激相关疾病而积累。尽管它们具有潜在的治疗价值，但文献中没有报道适当保护的ALE结构单元能够将其位点特异性掺入合成肽中。报道了Fmoc保护的ALE构件N 1-（3-甲基吡啶）赖氨酸（MP-赖氨酸）的合成及其掺入胶原模型肽中的报道。
• 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.