Reactions of 1,3-Diketones with a Dipeptide Isothiazolidin-3-one: Toward Agents That Covalently Capture Oxidized Protein Tyrosine Phosphatase 1B

Journal of Organic Chemistry

Volumn 80, Issue 24, 2015, Pages 12015-12026

  Ruddraraju, Kasi Viswanatharaju ^a   Parsons, Zachary D ^a   Llufrio, Elizabeth M ^a   Frost, Natasha L ^a   Gates, Kent S ^a,b  

^a UNIVERSITY OF MISSOURI   (United States)

^b University of Missouri   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDES; AMINO ACIDS; ENZYMES; INSULIN; OXIDATION; PEPTIDES; PHOSPHATASES; PROTEINS; SULFUR;

1 ,3-DIKETONES; COVALENT ATTACHMENT; INSULIN SIGNALING; INTRACELLULAR POOL; PROBE DESIGN; PROTEIN-TYROSINE PHOSPHATASE 1B; THERAPEUTIC TARGETS; TYPE-2 DIABETES;

CELL SIGNALING;

1,3 DIKETONE; 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [[2 (6 METHOXYNAPHTHALEN 2 YL) 2 OXOETHYL]THIO]PROPANAMIDO] 3 METHYLBUTANOATE; DIMETHYL 2 [[2 [(TERT BUTOXYCARBONYL)AMINO] 3 [(1 METHOXY 3 METHYL 1 OXOBUTAN 2 YL)AMINO] 3 OXOPROPYL]THIO]MALONATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [(1,3 DIOXO 1 PHENYLBUTAN 2 YL)THIO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [(1,3 DIOXO 1,3 DIPHENYLPROPAN 2 YL)THIO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [(2 HYDROXY 4 OXOPENT 2 EN 3 YL)THIO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [(2 HYDROXY 4,4 DIMETHYL 6 OXOCYCLOHEX 1 EN 1 YL)THIO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [(2 OXO 2 PHENYLETHYL)THIO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [(2 OXO 2 PHENYLETHYL)THIO]PROPANAMIDO]3 METHYLBUTANOATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [[1 (6 METHOXYNAPHTHALEN 2 YL) 1,3 DIOXOBUTAN 2 YL]THIO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [[2 (4 CHLOROPHENYL) 2 OXOETHYL]THIO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [[2 (NAPHTHALEN 2 YL) 2 OXOETHYL]THIO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [[2 OXO 2 (THIOPHEN 2 YL)ETHYL]THIO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [2 [(TERT BUTOXYCARBONYL)AMINO] 3 [[2 OXO 2 [4 (TRIFLUOROMETHYL)PHENYL]ETHYL]THIO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [3 [(2 ACETYL 1 OXO 1,2,3,4 TETRAHYDRONAPHTHA\LEN 2 YL)THIO] 2 [(TERT BUTOXYCARBONYL)AMINO]PROPANAMIDO] 3 METHYLBUTANOATE; METHYL 2 [[2 [(TERT BUTOXYCARBONYL)AMINO] 3 [(1 METHOXY 3 METHYL 1 OXOBUTAN 2 YL)AMINO] 3 OXOPROPYL]THIO] 3 HYDROXYBUT 2 ENOATE; PROTEIN TYROSINE PHOSPHATASE 1B INHIBITOR; UNCLASSIFIED DRUG; AMIDE; DIPEPTIDE; ENZYME INHIBITOR; ISOTHIAZOLIDINONE; KETONE; PROTEIN TYROSINE PHOSPHATASE 1B; PTPN1 PROTEIN, HUMAN; THIAZOLE DERIVATIVE;

ARTICLE; DRUG DESIGN; DRUG SYNTHESIS; ELECTROPHILICITY; INVESTIGATIVE PROCEDURES; NUCLEOPHILICITY; ANTAGONISTS AND INHIBITORS; CHEMISTRY; DIABETES MELLITUS, TYPE 2; ENZYMOLOGY; METABOLISM; OXIDATION REDUCTION REACTION;

AMIDES; DIABETES MELLITUS, TYPE 2; DIPEPTIDES; ENZYME INHIBITORS; KETONES; OXIDATION-REDUCTION; PROTEIN TYROSINE PHOSPHATASE, NON-RECEPTOR TYPE 1; THIAZOLES;

EID: 84952803332     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.5b01949     Document Type: Article

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