CRYSTAL AND MOLECULAR STRUCTURE OF L-AZETIDINE-2-CARBOXYLIC ACID . A NATURALLY OCCURRING HOMOLOG OF PROLINE

被引：70

作者：

BERMAN, HM

MCGANDY, EL

BURGNER, JW

VANETTEN, RL

机构：

[1] Department of Biochemistry and Nutrition, Graduate School of Public Health, Crystallography Laboratory, University of Pittsburgh, Pittsburgh

[2] Department of Biological Sciences, Department of Chemistry, Purdue University, Lafayette

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1969年 / 91卷 / 22期

关键词：

D O I：

10.1021/ja01050a044

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The crystal structure of L-azetidine-2-carboxylic acid (AzCOOH) has been determined by application of superposition methods using an E2-1 Patterson synthesis. The data were collected on a four-angle Picker automatic diffractometer using θ-2θ scan. The space group is P212121, with four molecules in a unit cell of dimensions a = 7.457, b = 9.810, and c = 6.328 Å. The molecule is in the zwitterionic form. Both hydrogen atoms on the nitrogen atom act as hydrogen-bonding donors to the oxygen atoms in neighboring molecules. The single hydrogen atom attached to the α carbon atom is a hydrogen-bond donor to a nearby carboxylate oxygen atom. The azetidine ring is buckled by 11 ° from a plane so that the carboxylate group lies farther from C(4), the distal ring carbon, than would be the case for a planar ring. The conformation of AzCOOH resembles those of proline and hydroxyproline, but its substitution for either of these amino acids in a polypeptide could bring about conformation changes sufficient to significantly alter the tertiary structure of the polypeptide. © 1969, American Chemical Society. All rights reserved.

引用

页码：6177 / &

共 30 条

[11] INHIBITION BY L-AZETIDINE-2-CARBOXYLIC ACID OF INDUCTION OF NITRATE REDUCTASE IN PLANTS AND ITS REVERSAL BY L-PROLINE [J].

HEWITT, EJ ;

NOTTON, BA .

PHYTOCHEMISTRY, 1967, 6 (10) :1329-&

[12]

Hughes E. W., 1941, J AM CHEM SOC, V63, P1737

[13]

JOHNSON CK, 1965, ORNL3794 REP

[14]

KAYUSHINA RL, 1966, SOV PHYS CRYSTALLOGR, V10, P698

[15] PRECISION SPACE-FILLING ATOMIC MODELS [J].

KOLTUN, WL .

BIOPOLYMERS, 1965, 3 (06) :665-&

[16] EFFETS DE DIFFERENTS ANALOGUES DE LA PROLINE SUR LE DEVELOPPEMENT DE LOEUF DE LOURSIN PARACENTROTUS LIVIDUS [J].

LALLIER, R .

EXPERIMENTAL CELL RESEARCH, 1965, 40 (03) :630-&

[17] THE CRYSTAL STRUCTURE OF L-LEUCYL-L-PROLYL-GLYCINE [J].

LEUNG, YC ;

MARSH, RE .

ACTA CRYSTALLOGRAPHICA, 1958, 11 (01) :17-31

[18] CRYSTAL AND MOLECULAR STRUCTURE OF N-METHYL-N-T-BUTYL-3-HYDROXYAZETIDINIUM METHANESULFONATE, A NONPLANAR AZETIDINIUM RING [J].

MCGANDY, EL ;

BERMAN, HM ;

BURGNER, JW ;

VANETTEN, RL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (22) :6173-&

[19] CRYSTAL AND MOLECULAR STRUCTURE OF 1-BENZYL-1,2,2-TRIMETHYL AZETIDINIUM BROMIDE [J].

MORET, CL ;

TREFONAS, LM .

JOURNAL OF HETEROCYCLIC CHEMISTRY, 1968, 5 (04) :549-&

[20] DIFFERENT SPECIFICITES OF PROLINE-ACTIVATING ENZYMES FROM SOME PLANT SPECIES [J].

PETERSON, PJ ;

FOWDEN, L .

NATURE, 1963, 200 (490) :148-+

← 1 2 3 →