Synthesis of lipid A monosaccharide analogues containing acidic amino acid: Exploring the structural basis for the endotoxic and antagonistic activities

Bioorganic and Medicinal Chemistry

Volumn 14, Issue 19, 2006, Pages 6759-6777

  Akamatsu, Masao ^a   Fujimoto, Yukari ^a   Kataoka, Mikayo ^a   Suda, Yasuo ^b   Kusumoto, Shoichi ^a   Fukase, Koichi ^a  

^a OSAKA UNIVERSITY   (Japan)

^b KAGOSHIMA UNIVERSITY   (Japan)

Author keywords

Cytokine induction; Endotoxin; IL 6; Innate immunity; Lipid A

Indexed keywords

ALLYL 4,6 O BENZYLIDENE 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; ALLYL 4,6 O BENZYLIDENE 3 O (3 BENZYLOXYTETRADECANOYL) 2 DEOXY 2 (2,2,2 TRICHLOROETHOXYCARBONYLAMINO) ALPHA DEXTRO GLUCOPYRANOSIDE; AMINO ACID; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 2 DEOXY 6 O [N (FLUORONYLMETHOXYCARBONYL) O TERT BUTYLSERYL] ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 2 DEOXY 6 O [N [(3 TETRADECANOYLOXY)TETRADECANOYL] DEXTRO SERYL] ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 2 DEOXY 6 O [N [3 (TETRADECANOYLOXY)TETRADECANOYL] O 4 BENZYL DEXTRO ASPARTYL] ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 2 DEOXY 6 O [N [3 (TETRADECANOYLOXY)TETRADECANOYL] O TERT BUTYL DEXTRO SERYL] ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 2 DEOXY 6 O [N [3 (TETRADECANOYLOXY)TETRADECANOYL] O TERT BUTYLSERYL] ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 2 DEOXY 6 O [N [3 (TETRADECANOYLOXY)TETRADECANOYL] SERYL] ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 6 O (N TERT BUTOXYCARBONYL O 4 BENZYL DEXTRO ASPARTYL) 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 6 O (N TERT BUTOXYCARBONYL O 4 BENZYLASPARTYL) 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 6 O [N (3 BENZYLOXYTETRADECANOYL) DEXTRO SERYL] 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 6 O [N (3 BENZYLOXYTETRADECANOYL) O 4 BENZYL DEXTRO ASPARTYL] 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 6 O [N (3 BENZYLOXYTETRADECANOYL) O 4 BENZYLASPARTYL] 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 6 O [N (3 BENZYLOXYTETRADECANOYL) O TERT BUTYL DEXTRO SERYL] 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 6 O [N (3 BENZYLOXYTETRADECANOYL) O TERT BUTYLSERYL] 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 6 O [N (3 BENZYLOXYTETRADECANOYL)SERYL] 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 6 O [N (3 HYDROXYTETRACARBONYL) O PHOSPHOSERYL] 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; BENZYLOXYCARBONYLMETHYL 4,6 O BENZYLIDENE 3 (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 2 DEOXY 2 ALPHA DEXTRO GLUCOPYRANOSIDE; CARBOXYLIC ACID; ENDOTOXIN; FORMYLMETHYL 4,6 O BENZYLIDENE 3 O (3 BENZYLOXYTETRADECANOYL) 2 (3 BENZYLOXYTETRADECANOYLAMINO) 2 DEOXY ALPHA DEXTRO GLUCOPYRANOSIDE; LIPID A DERIVATIVE; PHOSPHORIC ACID; UNCLASSIFIED DRUG;

ARTICLE; DRUG ACTIVITY; HUMAN; HUMAN CELL; NONHUMAN; PHOSPHORYLATION; SYNTHESIS;

ACYLATION; AMINO ACIDS, ACIDIC; BLOOD CELLS; DRUG DESIGN; ENDOTOXINS; HUMANS; INTERLEUKIN-6; LIMULUS TEST; LIPID A; LIPOPOLYSACCHARIDES; MAGNETIC RESONANCE SPECTROSCOPY; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 33747202835     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2006.05.051     Document Type: Article

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