Synthesis and ab initio conformational investigation of a series of model sulfated α-L-iduronopyranosides

Synthesis and ab initio conformational investigation of a series of model sulfated α-L-iduronopyranosides Full article

Journal

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

Output data

Year: 2024, Volume: 538, Article number : 109079, Pages count : DOI: 10.1016/j.carres.2024.109079

Authors

Tokatly Alexandra I. ¹ , Gerbst Alexey G. ¹ , Dmitrenok Andrey S. ¹ , Vinnitskiy Dmitry Z. ¹ , Nifantiev Nikolay E. ¹

Affiliations

1	Laboratory of Glycoconjugate Chemistry, N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospekt, 119991, Moscow, Russian Federation

Due to the all-axial orientation of the OH-groups in the 1C4 chair conformation considered standard for L-hexapyranosides, including l-iduronopyranoside – a component of many biologically and medically significant sulfated glycans, these monosaccharides can be anticipated to display unusual conformations upon the introduction of bulky and charged substituents. Herein we describe the synthesis of a series of iduronopyranoside derivatives with varying sulfation patterns, which were studied computationally using the DLPNO-MP2 approach and by means of analyzing their chemical shifts to ascertain the effects sulfation has on the conformation of the iduronopyranoside ring.

Tokatly A.I. , Gerbst A.G. , Dmitrenok A.S. , Vinnitskiy D.Z. , Nifantiev N.E.
Synthesis and ab initio conformational investigation of a series of model sulfated α-L-iduronopyranosides
Carbohydrate Research. 2024. V.538. 109079 . DOI: 10.1016/j.carres.2024.109079 WOS Scopus OpenAlex

≡ Web of science:	WOS:001221425400001
≡ Scopus:	2-s2.0-85187959689
≡ OpenAlex:	W4392678373