Upper rim appended hybrid calixarenes via click chemistry.
We report the application of "click" chemistry for the synthesis of hybrid calixarenes appended on the upper rim with carbohydrate and N,C-protected alpha-amino acids. The chemoselective N- or C-deprotection of the alpha-amino acids and their subsequent transformation into dipeptides is described. The first example of a chemo-enzymatic synthesis on upper rim derived calix[4]arenes using trans-sialidase affords sialylated lactose calix[4]arenes. Our innovative chemo-enzymatic process paves the way for further applications.
Bew
Sean P
SP
School of Chemical Sciences & Pharmacy, University of East Anglia, Norwich NR4 7TJ, UK. s.bew@uea.ac.uk
Brimage
Rebecca A
RA
L'Hermite
Nathalie
N
Sharma
Sunil V
SV
D000818:Animals; D047250:Calixarenes / Q000138:chemical synthesis* / Q000737:chemistry* / Q000378:metabolism; D002241:Carbohydrates / Q000737:chemistry; D006023:Glycoproteins / Q000378:metabolism; D008872:Microwaves; D015394:Molecular Structure; D009439:Neuraminidase / Q000378:metabolism; D014349:Trypanosoma cruzi / Q000201:enzymology
D002241:Carbohydrates; D006023:Glycoproteins; D047250:Calixarenes; C069715:trans-sialidase; D009439:Neuraminidase