Abstract
The heteroaromatic fused diazabicyclic “bimane” ring system, discovered four decades ago, is endowed with remarkable chemical and photophysical properties. No carbohydrate derivatives of bimanes have, however, been described thus far. Here we report on the syntheses of a range of bimanes decorated with various glycosyl residues. Mono- and disaccharide residues were attached to syn- or anti-bimane central cores via thio-, disulfido- or selenoglycosidic linkages to obtain novel fluorescent or nonfluorescent glycoconjugates. Cu(I)-catalyzed cycloaddition of glycosyl azides to a bimane diethynyl derivative furnished further bivalent glycoconjugates with sugar residues linked to the central bimane core via 1,2,3-triazole rings. We have determined the crystal and molecular structures of several glycosylated and non-glycosylated bimanes and report fluorescence data for the new compounds.
| Original language | English |
|---|---|
| Pages (from-to) | 88-98 |
| Number of pages | 11 |
| Journal | Carbohydrate Research |
| Volume | 473 |
| DOIs | |
| Publication status | Published - Feb 1 2019 |
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Keywords
- 1,2,3-triazole
- Disulfide
- Fluorescence
- Heteroaromatics
- Selenoglycoside
- Thioglycoside
- X-ray structures
ASJC Scopus subject areas
- Analytical Chemistry
- Biochemistry
- Organic Chemistry
Cite this
Bivalent glycoconjugates based on 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione (“bimane”) as a central scaffold. / Szabó, Tamás; Bényei, A.; Szilágyi, László.
In: Carbohydrate Research, Vol. 473, 01.02.2019, p. 88-98.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Bivalent glycoconjugates based on 1,5-diazabicyclo[3.3.0]octa-3,6-diene-2,8-dione (“bimane”) as a central scaffold
AU - Szabó, Tamás
AU - Bényei, A.
AU - Szilágyi, László
PY - 2019/2/1
Y1 - 2019/2/1
N2 - The heteroaromatic fused diazabicyclic “bimane” ring system, discovered four decades ago, is endowed with remarkable chemical and photophysical properties. No carbohydrate derivatives of bimanes have, however, been described thus far. Here we report on the syntheses of a range of bimanes decorated with various glycosyl residues. Mono- and disaccharide residues were attached to syn- or anti-bimane central cores via thio-, disulfido- or selenoglycosidic linkages to obtain novel fluorescent or nonfluorescent glycoconjugates. Cu(I)-catalyzed cycloaddition of glycosyl azides to a bimane diethynyl derivative furnished further bivalent glycoconjugates with sugar residues linked to the central bimane core via 1,2,3-triazole rings. We have determined the crystal and molecular structures of several glycosylated and non-glycosylated bimanes and report fluorescence data for the new compounds.
AB - The heteroaromatic fused diazabicyclic “bimane” ring system, discovered four decades ago, is endowed with remarkable chemical and photophysical properties. No carbohydrate derivatives of bimanes have, however, been described thus far. Here we report on the syntheses of a range of bimanes decorated with various glycosyl residues. Mono- and disaccharide residues were attached to syn- or anti-bimane central cores via thio-, disulfido- or selenoglycosidic linkages to obtain novel fluorescent or nonfluorescent glycoconjugates. Cu(I)-catalyzed cycloaddition of glycosyl azides to a bimane diethynyl derivative furnished further bivalent glycoconjugates with sugar residues linked to the central bimane core via 1,2,3-triazole rings. We have determined the crystal and molecular structures of several glycosylated and non-glycosylated bimanes and report fluorescence data for the new compounds.
KW - 1,2,3-triazole
KW - Disulfide
KW - Fluorescence
KW - Heteroaromatics
KW - Selenoglycoside
KW - Thioglycoside
KW - X-ray structures
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UR - http://www.scopus.com/inward/citedby.url?scp=85059851714&partnerID=8YFLogxK
U2 - 10.1016/j.carres.2019.01.002
DO - 10.1016/j.carres.2019.01.002
M3 - Article
VL - 473
SP - 88
EP - 98
JO - Carbohydrate Research
JF - Carbohydrate Research
SN - 0008-6215
ER -