Application of a Janus aglycon with dual function in benzyl-free synthesis of spacer-armed oligosaccharide fragments of polysaccharides from rhizobacterium Azospirillum brasilense sp7

Application of a Janus aglycon with dual function in benzyl-free synthesis of spacer-armed oligosaccharide fragments of polysaccharides from rhizobacterium Azospirillum brasilense sp7 Full article

Journal

Carbohydrate Research
ISSN: 1873-426X , E-ISSN: 0008-6215

Output data

Year: 2018, Volume: 464, Pages: 28-43 Pages count : 16 DOI: 10.1016/j.carres.2018.05.005

Authors

Abronina Polina I. ¹ , Zinin Alexander I. ¹ , Romashin Denis A. ¹ , Tereshina Valeria V. ¹ , Chizhov Alexander O. ¹ , Kononov Leonid O. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry of the Russian Academy of Sciences, Leninsky prosp. 47, 119991, Moscow, Russian Federation

Both protective and pre-spacer features of 4-(2-chloroethoxy)phenyl (CEP) aglycon, which belong to the class of Janus aglycons, were engaged in a benzyl-free synthesis of oligosaccharide fragments of polysaccharides from rhizobacterium Azospirillum brasilense sp7. Introduction of α-1,4-linked L-fucose residue was performed using 3,4-di-O-benzoyl-2-O-triisopropylsilyl-α-L-fucopyranosyl N-phenyltrifluoroacetimidate in excellent stereoselectivity and high yields. The obtained deprotected di-, tri- and tetrasaccharides contain 4-(2-azidoethoxy)phenyl (AEP) spacer aglycon, which allows straightforward preparation of neoglycoconjugates that will be used for the study of the role of lipopolysaccharide of rhizobacterium A. brasilense sp7 in plant–microbe symbiosis. The intermediate protected oligosaccharide building blocks with cleavable CEP/AEP aglycons have a strong potential for further application in the synthesis of more complex oligosaccharides.

Abronina P.I. , Zinin A.I. , Romashin D.A. , Tereshina V.V. , Chizhov A.O. , Kononov L.O.
Application of a Janus aglycon with dual function in benzyl-free synthesis of spacer-armed oligosaccharide fragments of polysaccharides from rhizobacterium Azospirillum brasilense sp7
Carbohydrate Research. 2018. V.464. P.28-43. DOI: 10.1016/j.carres.2018.05.005 WOS Scopus OpenAlex

Web of science:	WOS:000434788400006
Scopus:	2-s2.0-85047238644
OpenAlex:	W2803504940

DB	Citing
OpenAlex	22
Scopus	23
Web of science	23