Synthesis and biological evaluation of a chitobiose-based peptide VV-glycanase inhibitor library

Journal of Organic Chemistry

Volumn 74, Issue 2, 2009, Pages 605-616

  Witte, Martin D ^a   Horst, Danielle ^b   Wiertz, Emmanuel J H J ^b,c   Van Der Marel, Gijsbert A ^a   Overkleeft, Herman S ^a  

^a LEIDEN UNIVERSITY   (Netherlands)

^b LEIDEN UNIVERSITY MEDICAL CENTER   (Netherlands)

^c UNIVERSITY MEDICAL CENTER UTRECHT   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVE SITES; BIOLOGICAL EVALUATIONS; CHITOBIOSE; CHLOROMETHYL; CYSTEINE PROTEASE; CYSTEINE PROTEASE INHIBITORS; DEGLYCOSYLATION; N-LINKED;

KETONES; SUGARS;

AMINES;

1 BENZOYL 3 N [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYLCARBAMOYL]AZIRIDINE 2 CARBOXYLIC ACID ETHYL ESTER; 1 BENZOYL 3 N [O (2 ACETAMIDO 3 O BENZYL 4,6 O BENZYLIDENE 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYLCARBAMOYL]AZIRIDINE 2 CARBOXYLIC ACID ETHYL ESTER; 3 C [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL] 1 (2,6 DIMETHYLBENZOYLOXY)PROPAN 2 ONE; 3 C [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL] 1 METHANESULFONYLPROPENE; 3 C [O (2 ACETAMIDO 3 O BENZYL 4,6 O BENZYLIDENE 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL] 1 (2,6 DIMETHYLBENZOYLOXY)PROPAN 2 ONE; 3 C [O (2 ACETAMIDO 3 O BENZYL 4,6 O BENZYLIDENE 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL] 1 CHLOROPROPAN 2 ONE; 3 C [O (2 ACETAMIDO 3 O BENZYL 4,6 O BENZYLIDENE 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL] 1 HYDROXYPROPAN 2 ONE; 3 C [O (2 ACETAMIDO 3,4,6 TRI O ACETYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 3,6 DI O ACETYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL]PROPENE; 3 C [O (2 ACETAMIDO 3,4,6 TRI O ACETYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL]PROPENE; 3 C [O (2 ACETAMIDO 3,4,6 TRI O TERT BUTYLDIMETHYLSILYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 3,6 DI O TERT BUTYLDIMETHYLSILYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL] 1 METHANESULFONYLPROPENE; 3 C [O (2 ACETAMIDO 3,4,6 TRI O TERT BUTYLDIMETHYLSILYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 3,6 DI O TERT BUTYLDIMETHYLSILYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL]PROPENE; 3 C [O (3 O BENZYL 4,6 O BENZYLIDENE 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSYL) (1-4) 3,6 DI O BENZYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSYL]PROPENE; 3 C [O (3,4,6 TRI O ACETYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSYL) (1-4) 3,6 DI O BENZYL 2 DEOXY 2 PHTHALIMIDO BETA DEXTRO GLUCOPYRANOSYL]PROPENE; 3 N [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYLCARBAMOYL] AZIRIDINE 2 CARBOXYLIC ACID ETHYL ESTER; 3 N [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYLCARBAMOYL] OXIRANE 2 CARBOXYLIC ACID ETHYL ESTER; 3 N [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYLCARBAMOYL]AZIRIDINE 2 CARBOXYLIC ACID ETHYL ESTER; ACETAMIDE DERIVATIVE; CHITOBIOSE; CYSTEINE PROTEINASE INHIBITOR; ETHYL 4 C [O (2 ACETAMIDO 3,4,6 TRI O ACETYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 3,6 DI O ACETYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL] BUT 2 ENOATE; GLYCOPEPTIDASE; GLYCOSIDE; METHYL 4 C [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL] BUT 2 ENOATE; N [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL] 2,6 DIMETHYLBENZOYLOXYACETAMIDE; N [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL] FLUOROACETAMIDE; N [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL]MESYLOXYACETAMIDE; N [O (2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL]THIOPHENYLACETAMIDE; N [O (2 ACETAMIDO 3 O BENZYL 4,6 O BENZYLIDENE 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL) (1-4) 2 ACETAMIDO 3,6 DI O BENZYL 2 DEOXY BETA DEXTRO GLUCOPYRANOSYL]HYDROXYACETAMIDE; PEPTIDE LIBRARY; UNCLASSIFIED DRUG; UNINDEXED DRUG; ACETAMIDE; DISACCHARIDE; ENZYME INHIBITOR;

ARTICLE; BIOLOGICAL MONITORING; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; HUMAN; HUMAN CELL; SYNTHESIS; CELL LINE; CHEMISTRY; DRUG ANTAGONISM; ENZYME SPECIFICITY; IC 50; MOLECULAR LIBRARY;

ACETAMIDES; CELL LINE; CYSTEINE PROTEINASE INHIBITORS; DISACCHARIDES; ENZYME INHIBITORS; HUMANS; INHIBITORY CONCENTRATION 50; PEPTIDE-N4-(N-ACETYL-BETA-GLUCOSAMINYL) ASPARAGINE AMIDASE; SMALL MOLECULE LIBRARIES; SUBSTRATE SPECIFICITY;

EID: 60849105678     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801906s     Document Type: Article

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