TY - JOUR
T1 - Generation of molecular diversity on N-acetyllactosamine via O-cyanomethyl ethers
AU - Malet, Carles
AU - Hindsgaul, Ole
N1 - Funding Information:
This work was supported by the Natural Sciences and Engineering Research Council of Canada and by the Protein Engineering Network for Centers of Excellence.
PY - 1997/8/25
Y1 - 1997/8/25
N2 - The ability to generate molecular diversity around a natural carbohydrate ligand taking advantage of the rich chemistry of the nitrile functional group was demonstrated by synthesizing 24 derivatives of N-acetyllactosamine (LacNAc). The disaccharides prepared carried carboxymethyl, amidinomethyl, aminoethyl, and carbamoylmethyl substituents projecting from each of the six OH groups. The resulting LacNAc derivatives present new structural features with either negatively charged, positively charged, or polar-neutral small substituents sampling the entire periphery of the molecule. These new derivatives should be useful probes for studying carbohydrate-protein interactions in general, and for designing inhibitors of N-acetyllactosamine-binding proteins in particular.
AB - The ability to generate molecular diversity around a natural carbohydrate ligand taking advantage of the rich chemistry of the nitrile functional group was demonstrated by synthesizing 24 derivatives of N-acetyllactosamine (LacNAc). The disaccharides prepared carried carboxymethyl, amidinomethyl, aminoethyl, and carbamoylmethyl substituents projecting from each of the six OH groups. The resulting LacNAc derivatives present new structural features with either negatively charged, positively charged, or polar-neutral small substituents sampling the entire periphery of the molecule. These new derivatives should be useful probes for studying carbohydrate-protein interactions in general, and for designing inhibitors of N-acetyllactosamine-binding proteins in particular.
KW - Molecular diversity
KW - N-acetyllactosamine
KW - Sugar-analogs
UR - http://www.scopus.com/inward/record.url?scp=0030770064&partnerID=8YFLogxK
UR - https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=pure_univeritat_ramon_llull&SrcAuth=WosAPI&KeyUT=WOS:A1997XX92300006&DestLinkType=FullRecord&DestApp=WOS_CPL
U2 - 10.1016/S0008-6215(97)00142-0
DO - 10.1016/S0008-6215(97)00142-0
M3 - Article
AN - SCOPUS:0030770064
SN - 0008-6215
VL - 303
SP - 51
EP - 65
JO - Carbohydrate Research
JF - Carbohydrate Research
IS - 1
ER -