Synthesis of glycopeptide derivatives of Peptide T on a solid phase using an allylic linkage
✍ Scribed by Winfried Kosch; Joachim März; Horst Kunz
- Publisher
- Elsevier Science
- Year
- 1994
- Weight
- 1016 KB
- Volume
- 22
- Category
- Article
- ISSN
- 0923-1137
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📜 SIMILAR VOLUMES
t-Butyl 6-bromo-(E)-4-hexenoate was used as a handle for the solid-phase synthesis of glycopeptides. The handle was ®rst conjugated with Fmoc amino acids to form the allyl esters, which were then attached to the Sieber amide resin via acidic cleavage of the t-butyl esters followed by activation of t
The use of two dlfferent allylx "handles" has been mvcstlgated m the s&d-phase synthesis of protected peptldes Very iilgh ylcld3 for the cleavage ofpeptldes from the resin, under mdd condmons which preserve sidecham protcctmg groups can be achieved by caqmg out the cleavage reactmn m 2 2 1 THF/DMSO/
Different protective groups for (5R)-5-hydroxy-l-lysine were investigated in silver silicate promoted glycosylations with acetobromogalactose as glycosyl donor. Best results were obtained with Fmoc-Hyl(Cbz)-OAll, which was glycosylated in 80% yield. Removal of the allyl group gave a b-d-galactosylat
Phosphonium derivatives of HOAt such as PyAOP are useful for the solid-phase preparation of a range of peptides that include those incorporating hindered amino acids, difficult short sequences, and cyclic peptides. An advantage relative to uronium salts is that excess PyAOP does not undergo the detr