Conformation of 5-Amino-5-deoxypentonolactams

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Title:Conformation of 5-Amino-5-deoxypentonolactams
Creators:
Kefurt, Karel
Havlíček, Jaroslav
Hamerníková, Michaela
Kefurtová, Zdeňka
Votavová, Hana
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 62, 12, pp. 1919-1930
Uncontrolled Keywords:Circular dichroism, Lactams, Conformation analysis, Azasugars, NMR spectroscopy, Carbohydrates

Abstract

Four configuration isomers of 5-amino-5-deoxy-D-pentonolactam <strong>1a-4a</strong> and their tri-<i>O</i>-acetyl derivatives <strong>1b-4b</strong> were studied using NMR and CD spectroscopy. For all compounds chemical shifts of the <sup>1</sup>H and <sup>13</sup>C nuclei as well as of vicinal coupling constants were obtained. Comparison of the observed <sup>3</sup><i>J</i>(H,H) with those calculated for various conformations by a modified Karplus relationship led to the assignment of predominant conformation <sup>3</sup>H<sub>4</sub>(D) or <sup>4</sup>H<sub>3</sub>(D) to the lactams <strong>1a-4a</strong> and <strong>1b-4b</strong> in solution. The most important factor for determining the conformation seems to be the pseudoequatorial position of the substituent on the carbon next to the carbonyl group. The results of the CD spectra of the lactams <strong>1a-4a</strong> in water, interpreted according to the currently used rules, agreed with the NMR results.

Title:Conformation of 5-Amino-5-deoxypentonolactams
Creators:
Kefurt, Karel
Havlíček, Jaroslav
Hamerníková, Michaela
Kefurtová, Zdeňka
Votavová, Hana
Uncontrolled Keywords:Circular dichroism, Lactams, Conformation analysis, Azasugars, NMR spectroscopy, Carbohydrates
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:62
Number:12
Page Range:pp. 1919-1930
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19971919UNSPECIFIED
ID Code:1265
Item Type:Article
Deposited On:06 Feb 2009 17:08
Last Modified:06 Feb 2009 16:08

Citation

Kefurt, Karel; Havlíček, Jaroslav; Hamerníková, Michaela; Kefurtová, Zdeňka; Votavová, Hana (1997) Conformation of 5-Amino-5-deoxypentonolactams. Collection of Czechoslovak Chemical Communications, 62 (12). pp. 1919-1930. ISSN 0010-0765

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