The DOI matches its Crossref record; 1 of the 1 references it cites were found in a registry or an index.
Synthesis of Readily Modifiable Cyclodextrin Analogues via Cyclodimerization of an Alkynyl−Azido Trisaccharide
Abstract
A convergent strategy for the synthesis of beta-cyclodextrin analogues is reported, utilizing preferential cyclodimerization of an azido-alkyne trisaccharide via Cu(I)-catalyzed [3 + 2] dipolar cycloaddition of the alkyne and azide functional groups. The resultant oligosaccharide macrocycle retains the binding propensity of cyclodextrins, as demonstrated by the similar ANS association constants measured for macrocycle 1 and beta-cyclodextrin. This new synthetic strategy opens up new avenues for modular preparation of functionally diverse cyclodextrin analogues that are otherwise inaccessible.
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Citations
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Tornøe, C. W., Christensen, C., & Meldal, M. (2002) · The Journal of Organic Chemistry · doi:10.1021/jo011148j · Cited by 8,696
Cited by
CuI‐Catalyzed Alkyne–Azide “Click” Cycloadditions from a Mechanistic and Synthetic Perspective
Bock, V. D., Hiemstra, H., & van Maarseveen, J. H. (2006) · European Journal of Organic Chemistry · doi:10.1002/ejoc.200500483 · Cited by 1,452
Opsteen, J. A., & van Hest, J. C. M. (2005) · Chemical Communications · doi:10.1039/b412930j · Cited by 516
Cu(I)-Catalyzed Click Chemistry in Glycoscience and Their Diverse Applications
Agrahari, A. K., Bose, P., Jaiswal, M. K., Rajkhowa, S., Singh, A. S., Hotha, S., Mishra, N., & Tiwari, V. K. (2021) · Chemical Reviews · doi:10.1021/acs.chemrev.0c00920 · Cited by 445
Metadata
- Authors
- Bodine, K. D., Gin, D. Y., & Gin, M. S.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2004-01-27
- Volume
- 126
- Issue
- 6
- Pages
- 1638-1639
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2081396338
- Cited by
- 218
- References
- 1
- FWCI
- 11.65
- Type
- journal article
- Language
- en
- Open access
- closed
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