TY - JOUR
T1 - Exploring the self-assembly of glycopeptides using a diphenylalanine scaffold
AU - Roytman, Rinat
AU - Adler-Abramovich, Lihi
AU - Kumar, K. S.Ajish
AU - Kuan, Ting Chun
AU - Lin, Chun Cheng
AU - Gazit, Ehud
AU - Brik, Ashraf
PY - 2011/8/21
Y1 - 2011/8/21
N2 - Diphenylalanine, a key building block for organic nanotechnology, forms discrete, rigid and hollow nanotubes that are assembled spontaneously upon their dilution from organic phase into aqueous solution. Here we report the efficient preparation of several S-linked glycosylated diphenylalanine analogues bearing different monosaccharide, di-saccharide and sialic acid residues. The self-assembly studies revealed that these glycopeptides adopted various structures and glycosylation could be a tool to manipulate the self-assembly process. Moreover, the solubility of these analogues was found to be much greater than diphenylalanine, which could open new applications based on these nanostructures.
AB - Diphenylalanine, a key building block for organic nanotechnology, forms discrete, rigid and hollow nanotubes that are assembled spontaneously upon their dilution from organic phase into aqueous solution. Here we report the efficient preparation of several S-linked glycosylated diphenylalanine analogues bearing different monosaccharide, di-saccharide and sialic acid residues. The self-assembly studies revealed that these glycopeptides adopted various structures and glycosylation could be a tool to manipulate the self-assembly process. Moreover, the solubility of these analogues was found to be much greater than diphenylalanine, which could open new applications based on these nanostructures.
UR - http://www.scopus.com/inward/record.url?scp=79960987707&partnerID=8YFLogxK
U2 - 10.1039/c1ob05071k
DO - 10.1039/c1ob05071k
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AN - SCOPUS:79960987707
VL - 9
SP - 5755
EP - 5761
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
SN - 1477-0520
IS - 16
ER -