Naslov
Efficient synthesis of linear trisaccharide from QS- 21

Autori
Škalamera, Đani ; Tuković, Ivana

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
XII Young Investigator Workshop : Book of abstracts / - Barcelona : Societat Catalana de Química (SCQ) i EuChemS Divison of Organic Chemistry, 2021, 22-22

Skup
XII Young Investigator Workshop

Mjesto i datum
Barcelona, Španjolska, 25.11.2021. - 26.11.2021

Vrsta sudjelovanja
Pozvano predavanje

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Quillaja saponaria, immunoadjuvants, oligosaccharide synthesis

Sažetak
Adjuvants are key components of vaccines that improve and/or modulate the immune response to the applied antigen. The natural compound QS-21, a saponin isolated from the bark of Quillaja saponaria Molina tree, is one of the strongest known immunoadjuvants. However, QS-21 has a few major drawbacks which inhibit its wider use, e.g. chemical instability, accessibility and difficult purification ; which led to the development of QS- 21 derivatives and simpler variants. The linear trisaccharide Xyl(β1-4)Rha(α1-2)Fuc was found to be a crucial structural domain for the immunostimulatory activity of the QS-21 derivatives.1 Thus, its efficient synthesis is very important in the further development of QS-21 derivatives and analogs. Currently reported syntheses of the trisaccharide have shortcomings in extremely moisture-sensitive glycosylations, relatively high number of steps and low total yields.2 In this work, a simple, efficient and robust method of glycosylation using glycosyl fluorides as donors and silyl ethers as acceptors was used for the synthesis of trisaccharide Xyl(β1- 4)Rha(α1-2)Fuc. That led to the simplification of the synthetic pathway and reduction of the total number of steps, making the trisaccharide more easily accessible.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA