TY  - JOUR
A1  - Pavashe, Prashant
A1  - Elamparuthi, Elangovan
A1  - Hettrich, Cornelia
A1  - Moeller, Heiko M.
A1  - Linker, Torsten
T1  - Synthesis of 2-Thiocarbohydrates and Their Binding to Concanavalin A
JF  - The journal of organic chemistry
N2  - A convenient and general synthesis of 2-thiocarbohydrates via cerium ammonium nitrate oxidation of the thiocyanate ion is described. Radical addition to glycals proceeds with excellent regio- and good stereoselectivities in only one step, deprotection affords water-soluble 2-thio saccharides. Binding studies to Con A have been performed by isothermal titration calorimetry (ITC) and saturation transfer difference (STD) NMR spectroscopy. The 2-thiomannose derivative binds even stronger to Con A than the natural substrate, offering opportunities for new lectin or enzyme inhibitors.
Y1  - 2016
U6  - https://doi.org/10.1021/acs.joc.6b00987
SN  - 0022-3263
VL  - 81
SP  - 8595
EP  - 8603
PB  - American Chemical Society
CY  - Washington
ER  - 
TY  - JOUR
A1  - Elamparuthi, Elangovan
A1  - Linker, Torsten
A1  - Kelling, Alexandra
A1  - Schilde, Uwe
T1  - Crystal structure of methyl 3,4-di-O-benzyl-2-deoxy-2-C-nitromethyl-alpha-D-arabinopyranoside, C21H25NO6
Y1  - 2009
UR  - http://www.oldenbourg.de/verlag/zkristallogr/mn-ncsc.htm
U6  - https://doi.org/10.1524/ncrs.2009.0027
SN  - 1433-7266
ER  - 
TY  - JOUR
A1  - Elamparuthi, Elangovan
A1  - Linker, Torsten
T1  - Carbohydrate-2-deoxy-2-phosphonates : simple synthesis and Horner-Emmons reaction
N2  - Phosphorus meets carbohydrates: Dimethyl phosphite reacts with ceric(IV) ammonium nitrate (CAN) to give phosphonyl radicals that add to glycals 1. The derivatives 2 were isolated in high yields and during a subsequent Horner-Emmons reaction underwent an interesting elimination to give 3,6-dihydro-2H-pyrans 3. The short sequence with simple precursors is applicable to the transformation of hexoses, pentoses, and disaccharides. Bn=benzyl.
Y1  - 2009
UR  - http://onlinelibrary.wiley.com/journal/10.1002/(28ISSN)291521-3773
U6  - https://doi.org/10.1002/anie.200804725
SN  - 1433-7851
ER  -