Glycosylation of peptides using glycosyl phosphite reagents

Details Glycosylation of peptides using glycosyl phosphite reagents Glycosylation of peptides using glycosyl phosphite reagents

1993-03-18

1998-12-29

Tsang, Cecilia J.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Chemical aftertreatment, e.g., acylation, methylation, etc.

530340, 530322, C07K 1107

Patent

active

058543910

ABSTRACT:
A method for synthesizing glycosylated peptides employs a blocked carbohydrate donor and a blocked peptide acceptor. The carbohydrate donor includes an acid labile phosphite leaving group attached to the anomeric carbon. The blocked peptide acceptor includes an unprotected hydroxyl group susceptible to electrophilic attack. Serine hydroxyl is preferred. The reaction is initiated by the addition of a Lewis acid so as to activate the acid labile phosphite leaving group on the carbohydrate donor. The substitution reaction may be conducted at -78.degree. C. in a solvent such as Et.sub.3 N which favors the formation of glycosylated peptide products.

REFERENCES:
patent: 4719289 (1988-01-01), Kolar
Martin Tet Lett 33 6123 1992.
Ichikawa J Org Chem 57, 2943, 1992.
Perich Tet Lett 29, 2369 (1988).
Garg, Adv. Carbohydr. Chem. Biochem. 43, 135, 1985.
Kunz, Angew Chem Int. Ed, 26, 294, 1987.
Watanabe, Synlett 115, 1993.
Galpin Chemistry in Britain 14, 181, 1978.
Paulsen, Org. Synth.: Interdiscip. Challenge Proc. IUPAC Symp. 5th (1985) 317-335.
Flowers, Methods Enzymol 138, 359-404.

Affiliated with

Also associated with

Rating

Glycosylation of peptides using glycosyl phosphite reagents does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Glycosylation of peptides using glycosyl phosphite reagents, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Glycosylation of peptides using glycosyl phosphite reagents will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1425848