Boc-L-allo-Thr-OBn | 742060-65-7

• 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: Boc-L-allo-Thr-OBn
• 英文别名: N-Boc-L-allo-threonine benzyl ester；Benzyl N2-(tert-butoxycarbonyl)-L-allothreoninate；benzyl (2S,3S)-2-{[(tert-butoxy)carbonyl]amino}-3-hydroxybutanoate；benzyl (2S,3S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]butanoate
• CAS: 742060-65-7
• 化学式: C₁₆H₂₃NO₅
• 分子量: 309.362
• InChiKey: FHOGXXUNJQGWOP-AAEUAGOBSA-N

物化性质

• 沸点：
  464.0±40.0 °C(Predicted)
• 密度：
  1.152±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  22
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  Boc-L-allo-Thr-OBn 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 22.0h， 生成 (2S, 3S)-3-O-(pyrrole-2-carbonyloxy)-2-N-Boc-allo-threonine
  参考文献：
  名称：

  Tataricins A和B，两个新的来自Aster tataricus的环四肽及其绝对构型分配

  摘要：

  从传统中药紫t中分离出两个新颖的环四肽，他他汀A和B，具有独特的环肽主链和一个△2,4 Pro侧链。结合光谱数据，先进的Marfey方法和总合成方法确定了它们的结构和绝对构型。

  DOI：

  10.1016/j.tetlet.2012.12.111
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 碳酸氢钠 、 caesium carbonate 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 26.0h， 生成 Boc-L-allo-Thr-OBn
  参考文献：
  名称：

  Application of Serine- and Threonine-Derived Cyclic Sulfamidates for the Preparation of S-Linked Glycosyl Amino Acids in Solution- and Solid-Phase Peptide Synthesis

  摘要：

  Cyclic sulfamidates were synthesized in 60% yield from L-serine and allo-L-threonine, respectively. These sulfamidates reacted with a variety of unprotected 1-thio sugars in aqueous bicarbonate buffer (pH 8) to afford the corresponding S-linked serine- and threonine-glycosyl amino acids with good diastereo-selectivity (greater than or equal to97%) after hydrolysis of the A sulfates. The serine-derived sulfamidate was incorporated into a simple dlipeptide to generate a reactive dipeptide substrate that underwent chemoselective ligation with a 1-thio sugar to afford an S-linked glycopeptide. This sulfamidate was also incorporated into a peptide on a solid support in conjunction with solid-phase peptide synthesis. Chemoselective ligation of a 1-thio sugar with the cyclic sulfamidate was achieved on the solid support, followed by removal of the N-sulfate. Finally, the peptide chain of the resulting support-bound S-linked glycopeptide was extended using standard peptide synthesis procedures.

  DOI：

  10.1021/ja011932l

文献信息

• LYSOBACTIN AMIDES
  申请人：VON NUSSBAUM Franz

  公开号：US20090203582A1

  公开（公告）日：2009-08-13

  The invention relates to lysobactin amides and methods for their preparation, as well as their use for manufacturing medicaments for the treatment and/or prophylaxis of diseases, in particular bacterial infectious diseases.

  这项发明涉及赖氨酸胞素酰胺及其制备方法，以及它们用于制造治疗和/或预防疾病，特别是细菌感染性疾病的药物的用途。
• METHOD FOR PREPARING LYSOBACTIN DERIVATIVES
  申请人：VON NUSSBAUM Franz

  公开号：US20090163696A1

  公开（公告）日：2009-06-25

  Method for preparing cyclic depsipeptides having the following formula (I) by intramolecular cyclization.

  通过分子内环化制备具有以下式(I)的环状脱氨肽的方法。
• Structure and Total Synthesis of Lysobactin (Katanosin B)
  作者：Franz von Nussbaum、Sonja Anlauf、Jordi Benet-Buchholz、Dieter Häbich、Johannes Köbberling、László Musza、Joachim Telser、Helga Rübsamen-Waigmann、Nina A. Brunner

  DOI：10.1002/anie.200604232

  日期：2007.3.12
• Structure–activity relationships of globomycin analogues as antibiotics
  作者：Toshihiro Kiho、Mizuka Nakayama、Kayo Yasuda、Shunichi Miyakoshi、Masatoshi Inukai、Hiroshi Kogen

  DOI：10.1016/j.bmc.2003.10.055

  日期：2004.1

  Globomycin (1a), a signal peptidase II inhibitor, and its derivatives show potent antibacterial activity against Gram-negative bacteria. The synthesis and antimicrobial activity of novel globomycin analogues are reported. The hydroxyl group in the L-Ser residue was essential for the antimicrobial activity and the length of the alkyl side chain greatly influenced the activity. In addition, derivatives that had a modified cyclic core exhibited weak activity. One of the analogues showed a wider antimicrobial spectrum, effective against not only Gram-negative but also Gram-positive bacteria. (C) 2003 Elsevier Ltd. All rights reserved.
• LYSOBACTINAMIDE
  申请人：AiCuris GmbH & Co. KG

  公开号：EP2007794B1

  公开（公告）日：2011-09-14