𝔖 Bobbio Scriptorium
✦   LIBER   ✦

15N and 1H NMR study of ureido sugars, derivatives of 2-amino-2-deoxy-β-D-glucopyranosides

✍ Scribed by M. Weychert; J. Klimkiewicz; I. Wawer; B.Piekarska-Bartoszewicz; A. Temeriusz

Publisher
John Wiley and Sons
Year
1998
Tongue
English
Weight
209 KB
Volume
36
Category
Article
ISSN
0749-1581

No coin nor oath required. For personal study only.

✦ Synopsis

The 15N NMR spectra of a series of derivatives of 2-amino-2-deoxy-b-D-glucopyranose and dipeptides or secondary amines were recorded. In the dipeptide derivatives the chemical shift of nitrogen atom N-1 (linked to sugar) is essentially unchanged and the shifts of nitrogen atoms N-3 and N-6 are determined by the nature of the and substituents at C-a carbon of the amino acid unit. The highest shielding of N-3 and N-6 is R 1 R 2 observed for Gly units or and decreases in the order Gly

) of the nitrogen and proton of the N-6ÈH group results from the intramolecular hydrogen bonding interaction with the oxygen atom of the ester group. The experiment with HÈD isotopic exchange conÐrmed slow exchange of the N-6ÈH protons whereas the N-1ÈH and N-3ÈH protons, not involved in intramolecular H-bond, exchange fast.

📜 SIMILAR VOLUMES

Infrared and 1H NMR studies of hydrogen
Infrared and 1H NMR studies of hydrogen bonding in N-(2-amino-2-deoxy-β-D-glucopyranoside)-N′-carbamoyl-L-amino acid esters
✍ Monika Plass; Iwona Wawer; Boguslawa Piekarska-Bartoszewicz; Andrzej Temeriusz 📂 Article 📅 1997 🏛 John Wiley and Sons 🌐 English ⚖ 138 KB 👁 1 views

Ureido 2-deoxy-␤-D-glucopyranosides with seven different amino acid ester residues were studied by means of IR and 1 H NMR spectroscopy. The H-D exchange rates increase in the order L-Val <L-Leu <L-Ala < Gly for both NH protons; however, the exchange rate at N-1-H (linked to the glucopyranoside) is

NMR study of methyl 3,4,6-tri-O-acetyl-2
NMR study of methyl 3,4,6-tri-O-acetyl-2-deoxy-2-(alkylureido)-β-D-glucopyranosides
✍ Iwona Wawer; Małgorzata Weychert; Jan Klimkiewicz; Bogusława Piekarska-Bartoszew 📂 Article 📅 1999 🏛 John Wiley and Sons 🌐 English ⚖ 117 KB

Five derivatives of methyl 3,4,6-triacetyl-2-deoxy-(3@-dialkylureido)-b-D-glucopyranoside were studied by 1H and 13C, NMR spectroscopy in solutions and by 13C NMR spectroscopy in the solid state. Sterically CDCl 3 crowded substituents such as n-hexyl and cylcohexyl change the chemical shifts of H-1,

1H NMR Study of 2-Deoxy-D-Arabino-Hexopy
1H NMR Study of 2-Deoxy-D-Arabino-Hexopyranose (2-Deoxy Glucopyranose), 2-Deoxy-D-Lyxo-Hexopyranose (2-Deoxy Galactopyranose) and 2′-Deoxy Lactose. Shift Increment Studies in 2-Deoxy Carbohydrates
✍ A. De Bruyn; M. Anteunis 📂 Article 📅 2010 🏛 Wiley (John Wiley & Sons) ⚖ 287 KB

## Abstract Complete analyses of the ^1^H n.m.r. spectra at 300 MHz of D~2~0 solutions of 2‐deoxy‐D‐arabino‐hexopyranose, 2‐deoxy‐D‐lyxo‐hexopyranose and 2′‐deoxy lactose. Chemical shifts in the deoxy monosaccharides and in 2′‐deoxy lactose are compared with those previously obtained in the parent