An insight into the radical thiol/yne coupling: The emergence of arylalkyne-tagged sugars for the direct photoinduced glycosylation of cysteine-containing peptides

Journal of Organic Chemistry

Volumn 76, Issue 2, 2011, Pages 450-459

  Minozzi, Matteo ^a   Monesi, Alessandro ^a   Nanni, Daniele ^a   Spagnolo, Piero ^a   Marchetti, Nicola ^b   Massi, Alessandro ^b  

^a UNIVERSITY OF BOLOGNA   (Italy)

^b UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1-OCTYNE; ALKANETHIOLS; ALKYNYLS; AROMATIC ALKYNES; ARYL ACETYLENES; COUPLING PRODUCT; CYSTEINE-CONTAINING PEPTIDES; DERIVATIZATIONS; EQUIMOLAR AMOUNT; EXPERIMENTAL CONDITIONS; FUNCTIONALIZATIONS; GLUTATHIONES; HYDROTHIOLATION; N-ACETYL L-CYSTEINE; NATIVE FORMS; PHENYLACETYLENES; PHOTO-INDUCED; PHYSIOLOGICAL CONDITION; SELECTIVE PRODUCTION; THIOL-ENE COUPLING; TRIPEPTIDE;

ACETYLENE; AROMATIC HYDROCARBONS; ESTERIFICATION; ESTERS; GLYCOSYLATION; PEPTIDES; SUGAR (SUCROSE);

AMINO ACIDS;

1 OCTYNE; ALKYNE DERIVATIVE; CYSTEINE DERIVATIVE; GLUTATHIONE; GLYCOPEPTIDE; HEXYL 2,13 DIOXO 6,9 DITHIA 3,12 DIAZATETRADECANE 4,11 DICARBOXYLATE; METHYL 2 (OCT 1 ENYLTHIO)ACETATE; METHYL 2 [1 [(2 METHOXY 2 OXOETHYL)SULFANYL] 2 PHENYLETHYLSULFANYL]ACETATE; METHYL 2 [2 [(2 METHOXY 2 OXOETHYL)SULFANYL] 1 PHENYLETHYLSULFANYL]ACETATE; METHYL 2 [[1 [(2 METHOXY 2 OXOETHYL)SULFANYL]METHYLHEPTYL]SULFANYL]ACETATE; METHYL 2 ACETAMIDO 3 (OCT 1 ENYLTHIO)PROPANOATE; METHYL 2 ACETAMIDO 3 (STYRYLTHIO)PROPANOATE; PEPTIDE; PHENYLACETYLENE; SUGAR; TERT BUTYL [[(9H FLUOREN 9 YL)METHOXY]CARBONYLAMINO] 3 [3' (2'',3'',6'' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL) OXYPROP 1 ENYLTHIO]PROPANOATE; TERT BUTYL [[(9H FLUOREN 9 YL)METHOXY]CARBONYLAMINO] 3 [3' (2'',3'',6'' TETRA O ACETYL BETA DEXTRO GLUCOPYRANOSYL) OXYPROPAN 2' YLTHIO]PROPANOATE; THIOL; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; GLYCOSYLATION; ISOMERISM; STEREOCHEMISTRY;

CARBOHYDRATES; CYSTEINE; GLYCOPEPTIDES; GLYCOSYLATION; INDICATORS AND REAGENTS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PEPTIDES; PHOTOCHEMISTRY; STEREOISOMERISM; SULFHYDRYL COMPOUNDS;

EID: 78651503036     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101906j     Document Type: Article

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