(S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-tridecanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid allyl ester | 742060-66-8

• 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: (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-tridecanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid allyl ester
• CAS: 742060-66-8
• 化学式: C₅₁H₈₅N₅O₁₂
• 分子量: 960.262
• InChiKey: OCDZGLPJLISWSH-CPFNOSEOSA-N

反应信息

• 作为反应物：
  描述：

  (S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-tridecanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid allyl ester 在 吗啉 、 四(三苯基膦)钯 、 N,N-二异丙基乙胺 、 三氟乙酸 、 N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 生成 (6S,9S,12S,15S,18R,19R)-9-Benzyloxymethyl-12-((R)-sec-butyl)-19-decyl-6-((S)-1-hydroxy-ethyl)-15-isobutyl-16,18-dimethyl-1-oxa-4,7,10,13,16-pentaaza-cyclononadecane-2,5,8,11,14,17-hexaone
  参考文献：
  名称：

  Synthesis and antimicrobial activity of novel globomycin analogues

  摘要：

  Globomycin, 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. One of the analogues showed a more potent activity against Gram-negative bacteria than globomycin and also exhibited antibacterial activity against methicillin-resistant Staphylococcus aureus (MRSA). (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00432-3
• 作为产物：
  描述：

  N-((2R,3R)-3-[Boc-L-allo-Thr(TBS)-GlyO]-2-methyltridecanoyl)-N-Me-L-Leu-L-allo-Ile-L-Ser(Bn)-OAllyl 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 以91%的产率得到(S)-3-Benzyloxy-2-{(2S,3R)-2-[(S)-2-({(2R,3R)-3-[2-((2S,3S)-2-tert-butoxycarbonylamino-3-hydroxy-butyrylamino)-acetoxy]-2-methyl-tridecanoyl}-methyl-amino)-4-methyl-pentanoylamino]-3-methyl-pentanoylamino}-propionic acid allyl ester
  参考文献：
  名称：

  Structure–activity relationships of globomycin analogues as antibiotics

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2003.10.055