96095-04-4Relevant articles and documents
Simultaneous Determination of Absolute Configuration and Quantity of Lipopeptides Using Chiral Liquid Chromatography/Mass Spectrometry and Diastereomeric Internal Standards
Nemati, Reza,Dietz, Christopher,Anstadt, Emily,Clark, Robert,Smith, Michael,Nichols, Frank,Yao, Xudong
, p. 3583 - 3589 (2017/05/08)
Lipopeptides promote innate immune response and are related to disease pathology. To investigate the newly emerging roles of lipopeptides, accurate measurements of stereoisomers with multiple chiral 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 determining the absolute configuration and quantity of stereoisomers of bacteria-derived lipopeptides. Total lipid extracts of nine evaluated bacteria strains had different amounts, but only the (R)-isoform of l-serine-Lipid 654. The developed method also allowed for the first quantitative analysis of hydrolysis of a nonphospholipid as a novel substrate of honey bee venom phospholipase A2. (Graph Presented).
Structural verification via convergent total synthesis of dipeptide–lipids isolated from Porphyromonas gingivalis
Dietz, Christopher,Hart, Theresa K.,Nemati, Reza,Yao, Xudong,Nichols, Frank C.,Smith, Michael B.
, p. 7557 - 7569 (2016/11/11)
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.
Revised structure and synthesis of flavolipin
Shiozaki, Masao,Deguchi, Noriko,Mochizuki, Takashi,Wakabayashi, Takanori,Ishikawa, Tomio,Haruyama, Hideyuki,Kawai, Yohko,Nishijima, Masahiro
, p. 11861 - 11876 (2007/10/03)
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 synthesized in a stereocontrolled manner.
Revised structure of flavolipin and synthesis of its isomers
Shiozaki, Masao,Deguchi, Noriko,Ishikawa, Tomio,Haruyama, Hideyuki,Kawai, Yohko,Nishijima, Masahiro
, p. 4497 - 4500 (2007/10/03)
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.
Synthesis of topostins B567 and D654 (WB-3559D, flavolipin), DNA topoisomerase I inhibitors of bacterial origin
Shioiri, Takayuki,Terao, Yoshihiro,Irako, Naoko,Aoyama, Toyohiko
, p. 15701 - 15710 (2007/10/03)
Topostins B567 (2b) and D654 (3b) (WB-3559D, flavolipin) have been efficiently synthesized from 1,10-decanediol (5)in 11 and 13 steps, respectively, involving an asymmetric hydrogenation of the β-keto ester 14 using (R)-BINAp ruthenium bromide and a peptide coupling using diethyl phosphorocyanidate (DEPC, (EtO)2P(O)CN) as key steps.
N-Acylpeptide compound, processes for the preparation thereof and the pharmaceutical compositions
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, (2008/06/13)
This invention relates to new N-acylpeptide compounds of immunological activity, said compounds being of the formula: EQU1 wherein R1 and R2 are each alkyl or alkenyl; R3 is hydrogen, lower alkyl, hydroxy(lower)alkyl, heterocyclic(lower)alkyl or ar(lower)alkyl, wherein the aryl moiety may have hydroxy or protected hydroxy; R4 is carboxy, esterified carboxy, carboxy(lower)alkyl or esterified carboxy(lower)alkyl; X is bond or lower alkylene; Y is lower alkylene or lower alkylidene; and n is an integer of 0 to 1; or its pharmaceutically acceptable salt.
