ISSN:
0947-6539
Keywords:
bioorganic chemistry
;
carbohydrates
;
glycosides
;
peptide bonds
;
phytochemistry
;
Chemistry
;
General Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Two suitably protected building blocks (11 and 33) for the preparation of amide-linked heptaglucoside mimetic 2, an analogue of the naturally occurring phytoalexin elicitor 1a, were readily accessible by glycal chemistry. Sequential elongation of terminal glucuronide 21 with laminaribiosyl hemiaminal 33 and anomeric amine 11 by EDC/HOBt-catalyzed condensation and two-step conversion of the C6-OTr moiety into the corresponding carboxylate function afforded homogeneous carbopeptoid 2 in high overall yield. It was found that replacement of the acetal linkages by the more rigid amide bonds destroys the phytoalexin-elicitor activity.
Additional Material:
4 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/chem.19970030614