Synthesis and mass spectral characterization of mycobacterial phosphatidylinositol and its dimannosides

Journal of Organic Chemistry

Volumn 77, Issue 16, 2012, Pages 6743-6759

  Rankin, Gregory M ^a   Compton, Benjamin J ^b   Johnston, Karen A ^b   Hayman, Colin M ^b   Painter, Gavin F ^b   Larsen, David S ^a  

^a UNIVERSITY OF OTAGO   (New Zealand)

^b CALLAGHAN INNOVATION   (New Zealand)

Author keywords

[No Author keywords available]

Indexed keywords

CELL WALL LIPIDS; FRAGMENTATION PATTERNS; KEY FEATURE; LATE STAGE; LIPID EXTRACT; MASS SPECTRAL; MASS SPECTRAL FRAGMENTATION; MYCOBACTERIAL; NATURALLY OCCURRING; PHOSPHATIDYLINOSITOL; PROTECTING GROUP;

SPECTROSCOPIC ANALYSIS; SUGARS;

SPECTRUM ANALYZERS;

1 O (1 O ((R) 10 METHYLOCTADECANOYL) 2 O HEXADECANOYLSN GLYCERO 3 BENZYLPHOSPHORYL) 6 O (2,3,4,6 TETRA O BENZYLALPHA D MANNOPYRANOSYL) 2 O (2,3,4 TRI O BENZYL 6 O HEXADECANOYLALPHA D MANNOPYRANOSYL) 3,4,5 TRI O BENZYLD MYOINOSITOL; 1 O (1 O ((R) 10 METHYLOCTADECANOYL) 2 O HEXADECANOYLSN GLYCERO 3 PHOSPHORYL) D MYO INOSITOL; 1 O ALLYL 2 O (2 O BENZOYL 3,4 DI O BENZYL 6 O TRIISOPROPYLSILYLALPHA D MANNOPYRANOSYL) 6 O (2,3,4,6 TETRA O BENZYLALPHA D MANNOPYRANOSYL) 3,4,5 TRI O BENZYLD MYOINOSITOL; 1 O ALLYL 2 O (2 O METHOXYACETYL 3,4,6 TRI O BENZYLALPHA D MANNOPYRANOSYL) 6 O (2,3,4,6 TETRA O BENZYLALPHA D MANNOPYRANOSYL) 3,4,5 TRI O BENZYL D MYOINOSITOL; 1 O ALLYL 4,5 DI O BENZYL 3 O (4 (3,4 DIMETHOXYPHENYL)BENZYL) 6 O (2,3,4,6 TETRA O BENZYLALPHA D MANNOPYRANOSYL)D MYOINOSITOL; 2 O (2 O METHOXYACETYL 3,4,6 TRI O BENZYLALPHA D MANNOPYRANOSYL) 6 O (2,3,4,6 TETRA O BENZYLALPHA D MANNOPYRANOSYL) 3,4,5 TRI O BENZYL D MYOINOSITOL; 2 O BENZOYL 3,4 DI O BENZYL 6 O TERT BUTYLDIMETHYLSILYLALPHA D MANNOPYRANOSE; 2 O BENZOYL 3,4 DI O BENZYL 6 O TERT BUTYLDIMETHYLSILYLALPHA D MANNOPYRANOSYLTRICHLOROACETIMIDATE; 2 O BENZOYL 3,4 DI O BENZYLALPHA D MANNOPYRANOSE; 3 O (4 BROMOBENZYL) 1,2:4,5 DI O ISOPROPYLIDENE MYOINOSITOL; 3 O (4 BROMOBENZYL) 4,5 DI O BENZYL 6 O (2,3,4,6 TETRA O BENZYLALPHA D MANNOPYRANOSYL) 1,2 DI O ISOPROPYLIDENE D MYOINOSITOL; 3 O (4 BROMOBENZYL) 4,5 DI O BENZYL 6 O (2,3,4,6 TETRA O BENZYLALPHA D MANNOPYRANOSYL)D MYOINOSITOL; 3 O (4 BROMOBENZYL) 6 O (3,4,6 TRI O BENZYLALPHA D MANNOPYRANOSYL) 1,2:4,5 DI O ISOPROPYLIDENE D MYOINOSITOL; 3 O (4 BROMOBENZYL) 6 O (3,4,6 TRI O BENZYLALPHA D MANNOPYRANOSYL) 1,2:4,5 DI O ISOPROPYLIDENE L MYOINOSITOL; 4,5 DI O BENZYL 3 O (4 (3,4 DIMETHOXYPHENYL)BENZYL) 6 O (2,3,4,6 TETRA O BENZYLALPHA D MANNOPYRANOSYL)D MYOINOSITOL; 4,5 DIISOPROPYLIDENE D MYO INOSITOL; 6 O (2,3,4,6 TETRA O BENZYLALPHA D MANNOPYRANOSYL) 2 O (2,3,4 TRI O BENZYL 6 O HEXADECANOYLALPHA D MANNOPYRANOSYL) 3,4,5 TRI O BENZYLD MYOINOSITOL; 6 O (2,3,4,6 TETRA O BENZYLALPHA D MANNOPYRANOSYL) 2 O (2,3,4 TRI O BENZYLALPHA D MANNOPYRANOSYL) 3,4,5 TRI O BENZYLD MYOINOSITOL; 6 O ALPHA D MANNOPYRANOSYL 1 O (1 O ((R) 10 METHYLOCTADECANOYL) 2 O HEXADECANOYLSN GLYCERO 3 PHOSPHORYL) 2 O (6 O HEXADECANOYLALPHA D MANNOPYRANOSYL)D MYOINOSITOL; 6 O ALPHA D MANNOPYRANOSYL 2 O (2 O METHOXYACETYLALPHA D MANNOPYRANOSYL 1 O (1 O ((R) 10 METHYLOCTADECANOYL) 2 O HEXADECANOYLSN GLYCERO 3 PHOSPHORYL)D MYOINOSITOL; ANTIMYCOBACTERIAL AGENT; BENZYL (1 O ((R) 10 METHYLOCTADECANOYL) 2 O HEXADECANOYLSN GLYCERO)DIISOPROPYLPHOSPHORAMIDITE; DIBUTYL (2 O BENZOYL 3,4 DI O BENZYL 6 O TERT BUTYLDIMETHYLSILYLALPHA D MANNOPYRANOSYL)PHOSPHATE; DIMANNOSIDE DERIVATIVE; LIPID; MANNOSIDE; PHOSPHATIDYLINOSITOL; SODIUM 2,6 DI O ALPHA D MANNOPYRANOSYL 1 O (1 O ((R) 10 METHYLOCTADECANOYL) 2 O HEXADECANOYLSN GLYCERO 3 PHOSPHORYL)D MYOINOSITOL; TRIETHYLAMMONIUM 1 O ((R) 10 METHYLOCTADECANOYL) 2 O HEXADECANOYLSN GLYCERO 3 H PHOSPHONATE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ACYLATION; ARTICLE; CELL WALL; DRUG STRUCTURE; DRUG SYNTHESIS; FRAGMENTATION REACTION; MYCOBACTERIUM BOVIS; NONHUMAN; SPECTRAL SENSITIVITY;

CELL WALL; INOSITOL; MAGNETIC RESONANCE SPECTROSCOPY; MANNOSIDES; MOLECULAR WEIGHT; MYCOBACTERIUM BOVIS; PHOSPHATIDYLINOSITOLS; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION;

EID: 84865208298     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo301189y     Document Type: Article

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