Solution structure of R2Sn(IV)-β-N-Acetyl-Neuraminate (R=Me, Bu) complexes in D2O and DMSO-d6: experimental NMR and DFT computational study.

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Abstract

Two diorganotin(IV)–NANA complexes (NANA (1) = b-N-acetyl-Neuraminic Acid = 5-amino-3,5-dideoxy-D-glycero-b-D-galactononulosic acid) with formula Me2Sn(IV)NANA (2) and Bu2Sn(IV)NANA (3) were synthesized and characterized by 1H, 13C and 119Sn NMR spectroscopy, both in D2O and DMSO-d6 solutions. The experimental data in DMSO suggested the monosaccharide bidentate chelation via O1 carboxylate and vicinal O2 alkoxide atoms, which, in D2O, can be dynamically extended to a third binding site (O8 atom) of the pendant chain. Coordination at the tin atom is discussed on the basis of experimental NMR data and DFT calculation.
Lingua originaleEnglish
pagine (da-a)1440-1446
Numero di pagine7
RivistaDalton Transactions
Volume14
Stato di pubblicazionePublished - 2007

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Dimethyl Sulfoxide
Discrete Fourier transforms
Neuraminic Acids
Nuclear magnetic resonance
Atoms
Chelation
Nuclear magnetic resonance spectroscopy
Binding Sites
Acids
dimethyl(N-acetylneuraminic acid)tin(IV)

All Science Journal Classification (ASJC) codes

  • Inorganic Chemistry

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title = "Solution structure of R2Sn(IV)-β-N-Acetyl-Neuraminate (R=Me, Bu) complexes in D2O and DMSO-d6: experimental NMR and DFT computational study.",
abstract = "Two diorganotin(IV)–NANA complexes (NANA (1) = b-N-acetyl-Neuraminic Acid = 5-amino-3,5-dideoxy-D-glycero-b-D-galactononulosic acid) with formula Me2Sn(IV)NANA (2) and Bu2Sn(IV)NANA (3) were synthesized and characterized by 1H, 13C and 119Sn NMR spectroscopy, both in D2O and DMSO-d6 solutions. The experimental data in DMSO suggested the monosaccharide bidentate chelation via O1 carboxylate and vicinal O2 alkoxide atoms, which, in D2O, can be dynamically extended to a third binding site (O8 atom) of the pendant chain. Coordination at the tin atom is discussed on the basis of experimental NMR data and DFT calculation.",
author = "Nuccio Bertazzi and Lorenzo Pellerito and Francesco Ferrante and Girolamo Casella and Archimede Rotondo and Enrico Rotondo",
year = "2007",
language = "English",
volume = "14",
pages = "1440--1446",
journal = "Dalton Transactions",
issn = "1477-9226",
publisher = "Royal Society of Chemistry",

}

TY - JOUR

T1 - Solution structure of R2Sn(IV)-β-N-Acetyl-Neuraminate (R=Me, Bu) complexes in D2O and DMSO-d6: experimental NMR and DFT computational study.

AU - Bertazzi, Nuccio

AU - Pellerito, Lorenzo

AU - Ferrante, Francesco

AU - Casella, Girolamo

AU - Rotondo, Archimede

AU - Rotondo, Enrico

PY - 2007

Y1 - 2007

N2 - Two diorganotin(IV)–NANA complexes (NANA (1) = b-N-acetyl-Neuraminic Acid = 5-amino-3,5-dideoxy-D-glycero-b-D-galactononulosic acid) with formula Me2Sn(IV)NANA (2) and Bu2Sn(IV)NANA (3) were synthesized and characterized by 1H, 13C and 119Sn NMR spectroscopy, both in D2O and DMSO-d6 solutions. The experimental data in DMSO suggested the monosaccharide bidentate chelation via O1 carboxylate and vicinal O2 alkoxide atoms, which, in D2O, can be dynamically extended to a third binding site (O8 atom) of the pendant chain. Coordination at the tin atom is discussed on the basis of experimental NMR data and DFT calculation.

AB - Two diorganotin(IV)–NANA complexes (NANA (1) = b-N-acetyl-Neuraminic Acid = 5-amino-3,5-dideoxy-D-glycero-b-D-galactononulosic acid) with formula Me2Sn(IV)NANA (2) and Bu2Sn(IV)NANA (3) were synthesized and characterized by 1H, 13C and 119Sn NMR spectroscopy, both in D2O and DMSO-d6 solutions. The experimental data in DMSO suggested the monosaccharide bidentate chelation via O1 carboxylate and vicinal O2 alkoxide atoms, which, in D2O, can be dynamically extended to a third binding site (O8 atom) of the pendant chain. Coordination at the tin atom is discussed on the basis of experimental NMR data and DFT calculation.

UR - http://hdl.handle.net/10447/32542

UR - https://pubs.rsc.org/en/Content/ArticleLanding/2007/DT/B616330K#!divAbstract

M3 - Article

VL - 14

SP - 1440

EP - 1446

JO - Dalton Transactions

JF - Dalton Transactions

SN - 1477-9226

ER -