TY - JOUR

T1 - Synthesis of Aldose 11-Mercaptoundecanoyl Hydrazones as Promising Glycoligands of Noble Metal Nanoparticles

AU - Ershov, Andrei Y.

AU - Martynenkov, Alexander A.

AU - Lagoda, Igor V.

AU - Kopanitsa, Maria A.

AU - Yakimansky, Alexander V.

PY - 2019/11/28

Y1 - 2019/11/28

N2 - Thesynthetic method for previously unknown 11-mercaptoundecanoyl hydrazones of the aldose series (L-arabinose, D-ribose, D-xylose, L-rhamnose, L-fucose, D-mannose, D-galactose, D-glucose, N-acetyl-D-glucosamine, N-acetyl-D-mannosamine, D-lactose, D-maltose) was developed, and structures of the productes were determined. These compounds are perspective glycoligands for noble metal nanoparticles. The 1H and 13C NMR spectroscopy data show that most of these aldose 11-mercaptoundecanoyl hydrazones in DMSO-d6 solution exist as a tautomeric mixture of open hydrazone and cyclic pyranose forms. The linear hydrazone form is represented by a set of Z′,E′-conformational isomers, differing in the arrangement of substituents relative to the amide bond C–N, in comparable amounts. In the case of 11-mercaptoundecanoyl hydrazones derived from D-glucose, D-lactoseand D-maltose, the cyclic pyranose structure represented by α,β-configurational isomers is retained.

AB - Thesynthetic method for previously unknown 11-mercaptoundecanoyl hydrazones of the aldose series (L-arabinose, D-ribose, D-xylose, L-rhamnose, L-fucose, D-mannose, D-galactose, D-glucose, N-acetyl-D-glucosamine, N-acetyl-D-mannosamine, D-lactose, D-maltose) was developed, and structures of the productes were determined. These compounds are perspective glycoligands for noble metal nanoparticles. The 1H and 13C NMR spectroscopy data show that most of these aldose 11-mercaptoundecanoyl hydrazones in DMSO-d6 solution exist as a tautomeric mixture of open hydrazone and cyclic pyranose forms. The linear hydrazone form is represented by a set of Z′,E′-conformational isomers, differing in the arrangement of substituents relative to the amide bond C–N, in comparable amounts. In the case of 11-mercaptoundecanoyl hydrazones derived from D-glucose, D-lactoseand D-maltose, the cyclic pyranose structure represented by α,β-configurational isomers is retained.

KW - glycosylation

KW - hydrazones

KW - noble metal glycoligands

KW - tautomerism

KW - thiolated saccharides

UR - http://www.scopus.com/inward/record.url?scp=85075730565&partnerID=8YFLogxK

U2 - 10.1002/slct.201902942

DO - 10.1002/slct.201902942

M3 - Article

AN - SCOPUS:85075730565

VL - 4

SP - 12938

EP - 12941

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 44

ER -