(2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenylpropanoic acid | 487060-76-4

• 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: (2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenylpropanoic acid
• CAS: 487060-76-4
• 化学式: C₂₄H₂₁NO₅
• 分子量: 403.434
• InChiKey: UPEAXWJZGLFDFI-YADHBBJMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  95.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenylpropanoic acid 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 生成 threo-(2RS,3SR)-2-amino-3-hydroxy-3-phenylpropanoic acid hydrochloride
  参考文献：
  名称：

  Gymnangiamide, a Cytotoxic Pentapeptide from the Marine Hydroid Gymnangium regae

  摘要：

  A cytotoxic aqueous extract from the marine hydroid Gymnangium regae provided a novel linear pentapeptide, designated gymnangiamide (1). The planar structure of 1 was elucidated by interpretation of spectral data as well as chemical degradation and derivatization studies. In addition to the amino acids isoleucine and phenylserine, this peptide contained N-desmethyldolaisoleuine, O-desmethyldolaproine, and alpha-guanidino serine, three residues that have not previously been reported in a natural product. The absolute configurations of the constituent amino/guanidino acids were determined by chemical degradation and derivatization, followed by HPLC and LC-MS comparison with authentic standards. Gymnangiamide (1) was moderately cytotoxic against a number of human tumor cell lines in vitro.

  DOI：

  10.1021/jo0303113
• 作为产物：
  描述：

  (+/-)-methyl (βR)-β-hydroxy-1-phenylalaninate 在 盐酸 、 phosphate buffer 、 bovine pancreas α-chymotrypsin II 、 sodium acetate 、 sodium carbonate 作用下， 以 四氢呋喃 为溶剂， 反应 46.0h， 生成 (2R,3S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-hydroxy-3-phenylpropanoic acid
  参考文献：
  名称：

  Peptide inhibitors of CDK2-cyclin A that target the cyclin recruitment-Site: structural variants of the C-Terminal Phe

  摘要：

  A focused series of octapeptides based on the lead compound H-His-Ala-Lys-Arg-Arg-Leu-Ile-Phe-NH2 1, in which the C-terminal phenylalanine residue was replaced by alpha and/or beta-modified variants, was synthesized using solid-phase chemistry. Both the L-threo-beta-hydroxy-phenylalanine (beta-phenylserine, Pse) and (2S)-phenylalaninol derivatives, as competitive binders at the cyclin-recruitment site, displayed potent inhibitory activity towards the CDK2-cyclin A complex. Unexpectedly, the D-threo-Pse derivatives also showed inhibitory activity. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(02)00508-5

文献信息

• CO-AGONISTS OF THE GLUCAGON AND GLP-1 RECEPTORS
  申请人：MERCK SHARP & DOHME CORP.

  公开号：US20160114000A1

  公开（公告）日：2016-04-28

  Described are peptide analogs of glucagon, which have been modified to be resistant to cleavage and inactivation by dipeptidyl peptidase IV (DPP-IV) and to increase in vivo half-life of the peptide analog while enabling the peptide analog to have relatively balanced agonist activity at the glucagon-like peptide 1 (GLP-1) receptor and the glucagon (GCG) receptor, and the use of such GLP-1 receptor/GCG receptor co-agonists for treatment of metabolic disorders such as diabetes, non-alcoholic fatty liver disease (NAFLD), non-alcoholic steatohepatitis (NASH), and obesity.

  描述了胰高血糖素的肽类类似物，这些类似物经过改造，使其对二肽基肽酶IV（DPP-IV）的裂解和失活具有抵抗性，同时增加了肽类类似物在体内的半衰期，使肽类类似物能够在胰高血糖素样肽1（GLP-1）受体和胰高血糖素（GCG）受体上具有相对平衡的激动剂活性，并且利用这种GLP-1受体/GCG受体共激动剂治疗代谢性疾病，如糖尿病、非酒精性脂肪肝病（NAFLD）、非酒精性脂肪性肝炎（NASH）和肥胖症。
• Peptide inhibitors of CDK2-cyclin A that target the cyclin recruitment-Site: structural variants of the C-Terminal Phe
  作者：Gail E Atkinson、Angela Cowan、Campbell McInnes、Daniella I Zheleva、Peter M Fischer、Weng C Chan

  DOI：10.1016/s0960-894x(02)00508-5

  日期：2002.9

  A focused series of octapeptides based on the lead compound H-His-Ala-Lys-Arg-Arg-Leu-Ile-Phe-NH2 1, in which the C-terminal phenylalanine residue was replaced by alpha and/or beta-modified variants, was synthesized using solid-phase chemistry. Both the L-threo-beta-hydroxy-phenylalanine (beta-phenylserine, Pse) and (2S)-phenylalaninol derivatives, as competitive binders at the cyclin-recruitment site, displayed potent inhibitory activity towards the CDK2-cyclin A complex. Unexpectedly, the D-threo-Pse derivatives also showed inhibitory activity. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Gymnangiamide, a Cytotoxic Pentapeptide from the Marine Hydroid <i>Gymnangium</i> <i>r</i><i>egae</i>
  作者：Dennis J. Milanowski、Kirk R. Gustafson、Mohammad A. Rashid、Lewis K. Pannell、James B. McMahon、Michael R. Boyd

  DOI：10.1021/jo0303113

  日期：2004.4.1

  A cytotoxic aqueous extract from the marine hydroid Gymnangium regae provided a novel linear pentapeptide, designated gymnangiamide (1). The planar structure of 1 was elucidated by interpretation of spectral data as well as chemical degradation and derivatization studies. In addition to the amino acids isoleucine and phenylserine, this peptide contained N-desmethyldolaisoleuine, O-desmethyldolaproine, and alpha-guanidino serine, three residues that have not previously been reported in a natural product. The absolute configurations of the constituent amino/guanidino acids were determined by chemical degradation and derivatization, followed by HPLC and LC-MS comparison with authentic standards. Gymnangiamide (1) was moderately cytotoxic against a number of human tumor cell lines in vitro.