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Kärkkäinen, Tiina S., Kartha, K. P. Ravindranathan, MacMillan, Derek and Field, Robert A. 
ORCID: https://orcid.org/0000-0001-8574-0275
(2008)
Iodine-mediated glycosylation en route to mucin-related glyco-aminoacids and glycopeptides.
Carbohydrate Research, 343 (10-11).
pp. 1830-1834.
ISSN 0008-6215
Abstract
The use of iodine-DDQ as a promoter for glycosylation of Fmoc-Ser-OBn and Fmoc-Thr-OBn with phenylseleno 3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-d-galactopyranoside in toluene-dioxane gave 49% and 73% yields, respectively, of the corresponding α-glycosides as the sole glycoside products. Reductive acetylation of the azide groups and cleavage of the benzyl esters by hydrogenolysis gave building blocks that were used in solid-phase synthesis to prepare triglycosylated tetrapeptides (Ac3GalNAc-α-Ser)3-Gly and (Ac3GalNAc-α-Thr)3-Gly in 27% and 49% overall yield, respectively.
| Item Type: | Article |
|---|---|
| Additional Information: | Funding Information: This work was supported by the Association for International Cancer Research (studentship to T.S.K.) and the Royal Society (University Research Fellowship to D.M.). We thank the EPSRC Mass Spectrometry Service Centre, Swansea, for invaluable support. |
| Uncontrolled Keywords: | aminoacid,glycopeptide,glycosylation,iodine-ddq,mucin,phenyl selenoglycoside,analytical chemistry,biochemistry,organic chemistry ,/dk/atira/pure/subjectarea/asjc/1600/1602 |
| Faculty \ School: | Faculty of Science > School of Chemical Sciences and Pharmacy (former - to 2009) Faculty of Science > School of Biological Sciences |
| Related URLs: | |
| Depositing User: | LivePure Connector |
| Date Deposited: | 06 Sep 2024 13:35 |
| Last Modified: | 25 Sep 2024 18:07 |
| URI: | https://ueaeprints.uea.ac.uk/id/eprint/96606 |
| DOI: | 10.1016/j.carres.2008.03.034 |
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