(R)-1-((2-(((S)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)amino)-2-oxoethyl)amino)-15-methyl-1-oxohexadecan-3-yl 13-methyltetradecanoate | 103196-65-2

• 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: (R)-1-((2-(((S)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)amino)-2-oxoethyl)amino)-15-methyl-1-oxohexadecan-3-yl 13-methyltetradecanoate
• 英文别名: WB-3559 D methyl ester
• CAS: 103196-65-2
• 化学式: C₃₈H₇₂N₂O₇
• 分子量: 668.999
• InChiKey: FYNWUHZZJDRFET-NOCHOARKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  47.0
• 可旋转键数：
  32.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  131.03
• 氢给体数：
  3.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (R)-1-((2-(((S)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)amino)-2-oxoethyl)amino)-15-methyl-1-oxohexadecan-3-yl 13-methyltetradecanoate 在 potassium trimethylsilonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以74%的产率得到(3R)-N-<3-(13'-methyltetradecanoyloxy)-15-methylhexadecanoyl>glycyl-L-serine
  参考文献：
  名称：

  Structural verification via convergent total synthesis of dipeptide–lipids isolated from Porphyromonas gingivalis

  摘要：

  A periodontal pathogen, Porphyromonas gingivalis, produces two serine dipeptide lipid classes that we labeled lipid 654 and lipid 430, and both contain L-serine as the terminal amino acid. The lipid 654 and lipid 430 classes are each comprised of three species with differing fatty acid substitutions, but the most abundant species demonstrate unit masses of either 654 or 430, respectively. Recently we observed that the lipid 654 can be hydrolyzed by specific lipases to lipid 430. However, a substantial percentage of the naturally occurring lipid 654 cannot be enzymatically hydrolyzed to lipid 430. The observed partial hydrolysis could be due to the presence of a mixture of stereoisomers. Testing this theory requires structural verification of our so-called 654 and 430 by total synthesis. We present herein details of the convergent synthesis of lipids 430 and 654, which confirm the proposed structure of P. gingivalis lipid 654 to be (3R and 3S)-L-serine-2. The bis(fatty acid) (3R)-L-serine-2 was prepared as well as the synthetic precursor, serine dipeptide mono-fatty acid (3R)-L-serine-1, which is the structure of lipid 430. We also synthesized the (3S)-L-serine-2 diastereomer as well as (3S)-L-serine-1. Using these synthetic standards, we confirmed that PLA2-mediated hydrolysis of lipid 654 is enantioselective in that only the (3R)-L-serine-2, but not (3S)-L-serine 2 is enzymatically hydrolyzed. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.10.010
• 作为产物：
  描述：

  3-羟基-15-甲基十六烷酸酯 在 4-二甲氨基吡啶 、 2,6-二叔丁基-4-甲基苯酚 、 palladium on activated charcoal 、 四丁基氟化铵 、 氢气 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 二氯甲烷 为溶剂， 反应 174.25h， 生成 (R)-1-((2-(((S)-3-hydroxy-1-methoxy-1-oxopropan-2-yl)amino)-2-oxoethyl)amino)-15-methyl-1-oxohexadecan-3-yl 13-methyltetradecanoate
  参考文献：
  名称：

  Structural verification via convergent total synthesis of dipeptide–lipids isolated from Porphyromonas gingivalis

  摘要：

  A periodontal pathogen, Porphyromonas gingivalis, produces two serine dipeptide lipid classes that we labeled lipid 654 and lipid 430, and both contain L-serine as the terminal amino acid. The lipid 654 and lipid 430 classes are each comprised of three species with differing fatty acid substitutions, but the most abundant species demonstrate unit masses of either 654 or 430, respectively. Recently we observed that the lipid 654 can be hydrolyzed by specific lipases to lipid 430. However, a substantial percentage of the naturally occurring lipid 654 cannot be enzymatically hydrolyzed to lipid 430. The observed partial hydrolysis could be due to the presence of a mixture of stereoisomers. Testing this theory requires structural verification of our so-called 654 and 430 by total synthesis. We present herein details of the convergent synthesis of lipids 430 and 654, which confirm the proposed structure of P. gingivalis lipid 654 to be (3R and 3S)-L-serine-2. The bis(fatty acid) (3R)-L-serine-2 was prepared as well as the synthetic precursor, serine dipeptide mono-fatty acid (3R)-L-serine-1, which is the structure of lipid 430. We also synthesized the (3S)-L-serine-2 diastereomer as well as (3S)-L-serine-1. Using these synthetic standards, we confirmed that PLA2-mediated hydrolysis of lipid 654 is enantioselective in that only the (3R)-L-serine-2, but not (3S)-L-serine 2 is enzymatically hydrolyzed. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2016.10.010

文献信息

• Structure and synthesis of WB-3559 A, B, C and D, new fibrinolytic agents isolated from Flavobacterium sp.
  作者：Itsuo Uchida、Keizo Yoshida、Yoshio Kawai、Shigehiro Takase、Yoshikuni Itoh、Hirokazu Tanaka、Masanobu Kohsaka、Hiroshi Imanaka

  DOI：10.1248/cpb.33.424

  日期：——

  WB-3559 A, B, C, and D are new fibrinolytic agents isolated from Flavobacterium sp. No. 3559. The structure of these four compounds and the total synthesis of WB-3559 D are described.

  WB-3559 A、B、C 和 D 是从黄杆菌第 3559 号分离出来的新型纤维蛋白溶解剂。本文介绍了这四种化合物的结构以及 WB-3559 D 的全合成过程。