Studies on WB-3559 A,B,C and D, new potent fibrinolytic agents. II. Structure elucidation and synthesis.

Uchida, Isamu; Yoshida, Keizo; Kawai, Yoshio; Takase, Shigehiro; Itoh, Yoshikuni; Tanaka, Hirokazu; Kohsaka, Masanobu; Imanaka, Hiroshi

doi:10.7164/antibiotics.38.1476

Cited by 23 publications

(19 citation statements)

References 4 publications

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“…The synthesis of Flavolipin was carried out by sequential coupling of glycine benzyl ester 18 and l ‐serine benzyl ester 19 on the enantiopure branched acylated HFA 17 (Scheme ) …”

Section: Fahfas Are Endogenous Lipidsmentioning

confidence: 99%

“…The desired chiral alcohol function 20 came from enantiopure aldehyde 21 (derived from α‐ d ‐ribofuranose) . The saturated lipid chain was introduced by a Wittig elongation reaction with 11‐methyldodecyltriphenylphosphonium chloride followed by hydrogenation of the olefin using Adams's catalyst.…”

Section: Fahfas Are Endogenous Lipidsmentioning

confidence: 99%

“…Two strategies have been developed for acylation of the secondary alcohol from carboxylic acid 20 . While Uchida et al . firstly introduced the suitably protected glycine group (formation of amide 24 via hydroxyl‐succinimide activation) prior to the acylation of the secondary alcohol with 13‐methyl‐tetradecanoyl choride, Shiozaki et al .…”

Section: Fahfas Are Endogenous Lipidsmentioning

confidence: 99%

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Branched Fatty Acyl Esters of Hydroxyl Fatty Acids (FAHFAs), Appealing Beneficial Endogenous Fat against Obesity and Type‐2 Diabetes

Balas

Feillet‐Coudray

Durand

2018

Chemistry A European J

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After a brief overview of the biological significance of FAHFAs, the present Minireview highlights the different strategies developed for their chemical syntheses. The term "FAHFAs" has been introduced in 2014 for fatty acyl esters of hydroxyl fatty acids, found in adipocytes, with antidiabetic properties. However, many other natural products contain this type of branched lipids in their structure. This review was then extended to the synthesis of these subunits, even though the length of the lipid chains and the location of the ester linkages are different, since the developed strategies may be applied to the synthesis of "FAHFA".

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“…The synthesis of Flavolipin was carried out by sequential coupling of glycine benzyl ester 18 and l ‐serine benzyl ester 19 on the enantiopure branched acylated HFA 17 (Scheme ) …”

Section: Fahfas Are Endogenous Lipidsmentioning

confidence: 99%

Section: Fahfas Are Endogenous Lipidsmentioning

confidence: 99%

Section: Fahfas Are Endogenous Lipidsmentioning

confidence: 99%

See 1 more Smart Citation

Branched Fatty Acyl Esters of Hydroxyl Fatty Acids (FAHFAs), Appealing Beneficial Endogenous Fat against Obesity and Type‐2 Diabetes

Balas

Feillet‐Coudray

Durand

2018

Chemistry A European J

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“…1), is unique to Flavobacterium spp. and comprises ϳ20% of the cellular lipids of Flavobacterium meningosepticum (1,7). F. meningosepticum is an opportunistic pathogen that causes pneumonia, meningitis, and septicemia in immunocompromised individuals, such as newborn infants and patients with advanced HIV disease (8 -11).…”

Section: Toll-like Receptor 4-md-2 Complex Mediates the Signalmentioning

confidence: 99%

Toll-Like Receptor 4-MD-2 Complex Mediates the Signal Transduction Induced by Flavolipin, an Amino Acid-Containing Lipid Unique toFlavobacterium meningosepticum

Gomi

Kawasaki

Kawai

et al. 2002

The Journal of Immunology

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Flavolipin, an amino acid-containing lipid isolated from Flavobacterium meningosepticum, induces many immune responses. It has been shown that flavolipin does not induce an immune response of macrophages derived from C3H/HeJ mice, which possess a point mutation in Toll-like receptor 4 (TLR4). To determine whether TLR4 or the molecular complex of TLR4 and TLR4 association molecule MD-2 mediates the flavolipin signal, flavolipin responsiveness was examined by measuring NF-κB activation in Ba/F3 cells and Ba/F3 transfectants expressing TLR4 or both TLR4 and MD-2. Flavolipin-induced NF-κB activation was detected in the cells expressing both TLR4 and MD-2, but not in the other cells. Expression of CD14 in the transfectant expressing both TLR4 and MD-2 increased the sensitivity to flavolipin. Furthermore, flavolipin stereoisomers were chemically synthesized, and their abilities to induce NF-κB activation were examined. (R)-Flavolipin, in which the configuration of the lipid moiety is R, induced NF-κB activation via the TLR4-MD-2 complex, but (S)-flavolipin did not. In this study, we demonstrated the involvement of TLR4-MD-2 and CD14 in flavolipin signaling and the importance of the (R)-configuration of the flavolipin lipid moiety for the induction of an immune response via TLR4-MD-2.

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“…16 Flavolipin, which contains serine and glycine, is unique to Flavobacterium spp., and comprises about 20% of the cellular lipids of Flavobacterium meningosepticum. 11,17 Flavolipin has been shown to induce inflammatory immune responses, such as PGE 2 , IL-1b and TNF-a production by macrophages. 18 The cellular receptor and signaling molecules for flavolipin have not been characterized well, and the essential moiety of flavolipin for the induction of an immune response has not been determined yet.…”

Section: Introductionmentioning

confidence: 99%

Molecular basis for lipopolysaccharide mimetic action of Taxol<SUP>™</SUP> and flavolipin

Kawasaki¹,

Gomi²,

Kawai³

et al. 2003

J. Endotoxin Res.

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We previously reported that Taxol, which mimics the action of LPS on murine macrophages, induces signals via mouse TLR4/MD-2, but not via human TLR4/MD-2. Here we investigated the molecular basis for this species-specific action of Taxol. Expression of mouse MD-2 conferred both LPS and Taxol responsiveness on HEK293 cells expressing mouse TLR4, whereas expression of human MD-2 conferred LPS responsiveness alone, suggesting that MD-2 is responsible for the species-specificity of Taxol responsiveness. Furthermore, mouse MD-2 mutants, in which Gln-22 was changed to other amino acids, showed dramatically reduced ability to confer Taxol responsiveness, although their ability to confer LPS responsiveness was not affected. These results indicated that Gln-22 of mouse MD-2 is essential for Taxol signaling, but not for LPS signaling. In this study, we also found that the TLR4/MD-2 complex, together with CD14, mediated signal transduction induced by flavolipin, an amino acid-containing lipid unique to Flavobacterium meningosepticum.

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Studies on WB-3559 A,B,C and D, new potent fibrinolytic agents. II. Structure elucidation and synthesis.

Cited by 23 publications

References 4 publications

Branched Fatty Acyl Esters of Hydroxyl Fatty Acids (FAHFAs), Appealing Beneficial Endogenous Fat against Obesity and Type‐2 Diabetes

Branched Fatty Acyl Esters of Hydroxyl Fatty Acids (FAHFAs), Appealing Beneficial Endogenous Fat against Obesity and Type‐2 Diabetes

Toll-Like Receptor 4-MD-2 Complex Mediates the Signal Transduction Induced by Flavolipin, an Amino Acid-Containing Lipid Unique toFlavobacterium meningosepticum

Molecular basis for lipopolysaccharide mimetic action of Taxol<SUP>™</SUP> and flavolipin

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