Fmoc-Thr(tBu)-Gly-OAll | 1429504-49-3

• 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-Thr(tBu)-Gly-OAll
• 英文别名: Fmoc-Thr(tBu)-Gly-Oallyl；prop-2-enyl 2-[[(2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3-[(2-methylpropan-2-yl)oxy]butanoyl]amino]acetate
• CAS: 1429504-49-3
• 化学式: C₂₈H₃₄N₂O₆
• 分子量: 494.588
• InChiKey: YLMOWBKSURTOST-CJAUYULYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Fmoc-Thr(tBu)-Gly-OAll 在 咪唑 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.5h， 生成 Fmoc-Thr(TBDMS)-Gly-Oallyl
  参考文献：
  名称：

  Total Synthesis of Daptomycin by Cyclization via a Chemoselective Serine Ligation

  摘要：

  A total synthesis of daptomycin, the first natural product antibiotic launched in a generation, was achieved. This convergent synthesis relies on an efficient macrocyclization via a serine ligation to assemble the 31-membered cyclic depsipeptide. The difficult esterification by the nonproteinogenic amino acid kynurenine was accomplished via the esterification of a threonine residue by a suitably protected Trp ester, followed by ozonolysis. This synthesis provides a foundation and framework to prepare varied analogues of daptomycin to establish its structure-activity profile.

  DOI：

  10.1021/ja4012468
• 作为产物：
  描述：

  Boc-Gly-OAll 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.5h， 生成 Fmoc-Thr(tBu)-Gly-OAll
  参考文献：
  名称：

  Total Synthesis of Daptomycin by Cyclization via a Chemoselective Serine Ligation

  摘要：

  A total synthesis of daptomycin, the first natural product antibiotic launched in a generation, was achieved. This convergent synthesis relies on an efficient macrocyclization via a serine ligation to assemble the 31-membered cyclic depsipeptide. The difficult esterification by the nonproteinogenic amino acid kynurenine was accomplished via the esterification of a threonine residue by a suitably protected Trp ester, followed by ozonolysis. This synthesis provides a foundation and framework to prepare varied analogues of daptomycin to establish its structure-activity profile.

  DOI：

  10.1021/ja4012468

文献信息

• DAPTOMYCIN ANALOGUES AND A METHOD FOR THE PREPARATION OF DAPTOMYCIN OR A DAPTOMYCIN ANALOGUE
  申请人：THE UNIVERSITY OF HONG KONG

  公开号：US20150126707A1

  公开（公告）日：2015-05-07

  A method for the synthesis of daptomycin or a daptomycin analogue is carried out on a resin to form a linear precursor followed by a serine ligation macrocyclization in solution. Daptomycin analogues can differ from daptomycin by substitution of amino acids residues and/or deletion or addition of amino acid residues. Daptomycin analogues can include a different fatty acid in the side arm of the daptomycin analogue.

  一种合成达托霉素或达托霉素类似物的方法在树脂上进行，形成线性前体，然后在溶液中进行丝氨酸连接的大环化反应。达托霉素类似物可以通过替换氨基酸残基和/或删除或添加氨基酸残基与达托霉素不同。达托霉素类似物的侧链中可以包含不同的脂肪酸。
• Total Synthesis of Daptomycin by Cyclization via a Chemoselective Serine Ligation
  作者：Hiu Yung Lam、Yinfeng Zhang、Han Liu、Jianchao Xu、Clarence T. T. Wong、Ci Xu、Xuechen Li

  DOI：10.1021/ja4012468

  日期：2013.4.24

  A total synthesis of daptomycin, the first natural product antibiotic launched in a generation, was achieved. This convergent synthesis relies on an efficient macrocyclization via a serine ligation to assemble the 31-membered cyclic depsipeptide. The difficult esterification by the nonproteinogenic amino acid kynurenine was accomplished via the esterification of a threonine residue by a suitably protected Trp ester, followed by ozonolysis. This synthesis provides a foundation and framework to prepare varied analogues of daptomycin to establish its structure-activity profile.