((S)-15-methyl-3-((13-methyltetradecanoyl)oxy)hexadecanoyl)glycyl-L-serine

• 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)-15-methyl-3-((13-methyltetradecanoyl)oxy)hexadecanoyl)glycyl-L-serine
• 英文别名: (3S)-(15-methyl-3-((13-methyltetradecanoyl)oxy)hexadecanoyl)glycyl-L-serine；(2S)-3-hydroxy-2-[[2-[[(3S)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]amino]acetyl]amino]propanoic acid
• 化学式: C₃₇H₇₀N₂O₇
• 分子量: 654.972
• InChiKey: DZKPDDDIBSEKLY-LQJZCPKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  11.1
• 重原子数：
  46
• 可旋转键数：
  33
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  142
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  13-甲基十四烷酸 在 palladium dihydroxide 、 palladium on activated charcoal 4-二甲氨基吡啶 、 草酰氯 、 氢气 、 三乙胺 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 26.5h， 生成 ((S)-15-methyl-3-((13-methyltetradecanoyl)oxy)hexadecanoyl)glycyl-L-serine
  参考文献：
  名称：

  黄酮磷脂的修订结构与合成

  摘要：

  通过合成研究和生物学活性测试，将天然黄酮素的拟议结构修订为N- [ N -[（3 R）-15-甲基-3-（13-甲基十四烷氧基）十六烷酰基]甘氨酰] -L-丝氨酸。 ，其异构体以立体控制的方式合成。

  DOI：

  10.1016/s0040-4020(98)83044-5

文献信息

• Revised structure and synthesis of flavolipin
  作者：Masao Shiozaki、Noriko Deguchi、Takashi Mochizuki、Takanori Wakabayashi、Tomio Ishikawa、Hideyuki Haruyama、Yohko Kawai、Masahiro Nishijima

  DOI：10.1016/s0040-4020(98)83044-5

  日期：1998.9

  The proposed structure of natural flavolipin was revised as N-[N-[(3R)-15-methyl-3- (13-methyltetradecanoyloxy)hexadecanoyl]glycyl]-L-serine as a result of a synthetic study and biological activity tests, and its isomers were synthesized in a stereocontrolled manner.

  通过合成研究和生物学活性测试，将天然黄酮素的拟议结构修订为N- [ N -[（3 R）-15-甲基-3-（13-甲基十四烷氧基）十六烷酰基]甘氨酰] -L-丝氨酸。 ，其异构体以立体控制的方式合成。
• Revised structure of flavolipin and synthesis of its isomers
  作者：Masao Shiozaki、Noriko Deguchi、Tomio Ishikawa、Hideyuki Haruyama、Yohko Kawai、Masahiro Nishijima

  DOI：10.1016/s0040-4039(98)00798-9

  日期：1998.6

  The proposed structure of natural flavolipin was revised as N-[N-[(3R)-15-methyl-3-(13-methyltetradecanoyloxy)hexadecanoyl]glycyl]-L-serine as a result of synthetic study and biological activity test.

  通过合成研究和生物学活性测试的结果，将天然黄素的拟议结构修改为N- [N-[（3R）-15-甲基-3-（13-甲基十四烷酰氧基）十六烷酰基]甘氨酰] -L-丝氨酸。
• Simultaneous Determination of Absolute Configuration and Quantity of Lipopeptides Using Chiral Liquid Chromatography/Mass Spectrometry and Diastereomeric Internal Standards
  作者：Reza Nemati、Christopher Dietz、Emily Anstadt、Robert Clark、Michael Smith、Frank Nichols、Xudong Yao

  DOI：10.1021/acs.analchem.6b04901

  日期：2017.3.21

  centers are essential yet challenging. This work uses (3R)- and (3S)-(15-methyl-3-((13-methyltetradecanoyl)oxy)hexadecanoyl)glycyl-l-serine, abbreviated as l-serine-(R+S)-Lipid 654, to develop a method that combines chiral liquid chromatography, a diastereomeric mixture of isotopically labeled internal standards, and multiple reaction monitoring mass spectrometry. The new method allows for simultaneously

  脂肽促进先天免疫应答，并与疾病病理学有关。为了研究脂肽的新兴作用，具有多个手性中心的立体异构体的准确测量是必不可少的，但是具有挑战性。这项工作使用（3 R）-和（3 S）-（15-甲基-3-（（13-甲基十四烷氧基）氧基）十六烷酰基）甘氨酰-1-丝氨酸，缩写为1-丝氨酸-（R + S-Lipid 654，以开发一种将手性液相色谱法，同位素标记的内标物的非对映异构体混合物和多反应监测质谱法相结合的方法。新方法允许同时确定细菌衍生脂肽的立体异构体的绝对构型和数量。九种评估细菌菌株的总脂质提取物含量不同，但只有1-丝氨酸-脂质654的（R）-亚型。开发的方法还允许对非磷脂作为蜜蜂新型底物的水解进行首次定量分析。毒磷脂酶A2。
• Structural verification via convergent total synthesis of dipeptide–lipids isolated from Porphyromonas gingivalis
  作者：Christopher Dietz、Theresa K. Hart、Reza Nemati、Xudong Yao、Frank C. Nichols、Michael B. Smith

  DOI：10.1016/j.tet.2016.10.010

  日期：2016.11

  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.