Crystal Structures of Cyclosporin Derivatives: O-Acetyl-(4R)-4-(E-2-butyl)-4,N-dimethyl-L-threonyl-cyclosporin A and O-Acetyl-(4R)-4-[E-2-(4-bromobutyl)]-4,N-dimethyl-L-threonyl-cyclosporin A

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Title:Crystal Structures of Cyclosporin Derivatives: O-Acetyl-(4R)-4-(E-2-butyl)-4,N-dimethyl-L-threonyl-cyclosporin A and O-Acetyl-(4R)-4-[E-2-(4-bromobutyl)]-4,N-dimethyl-L-threonyl-cyclosporin A
Creators:
Kratochvíl, Bohumil
Jegorov, Alexandr
Pakhomova, Svetlana
Hušák, Michal
Bulej, Petr
Cvak, Ladislav
Sedmera, Petr
Havlíček, Vladimír
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 64, 1, pp. 89-98
Uncontrolled Keywords:Cyclic peptides, X-Ray diffraction, Immunosupressants, Crystal structure determination, Cyclosporins, NMR spectroscopy

Abstract

The structures of <i>O</i>-acetyl-(4<i>R</i>)-4-(<i>E</i>-2-butyl)-4,<i>N</i>-dimethyl-L-threonyl-cyclosporin A (<strong>1</strong>) and <i>O</i>-acetyl-(4<i>R</i>)-4-[<i>E</i>-2-(4-bromobutyl)]-4,<i>N</i>-dimethyl-L-threonyl-cyclosporin A (<strong>2</strong>) were determined by X-ray diffraction methods and compared with the structure of related cyclosporins. In contrast to expectation, neither the acetylation nor the subsequent bromination of <strong>1</strong> affects the conformation and packing of cyclosporins in the solid state. Both compounds are isomorphous and crystallize in the orthorhombic space group <i>P2</i><sub>1</sub><i>2</i><sub>1</sub><i>2</i><sub>1</sub> with <i>a</i> = 12.936(2) Å, <i>b</i> = 15.590(2) Å, <i>c</i> = 36.280(3) Å, and <i>a</i> = 12.916(3) Å, <i>b</i> = 15.675(4) Å, <i>c</i> = 36.715(7) Å, for <strong>1</strong> and <strong>2</strong>, respectively. <p>

Title:Crystal Structures of Cyclosporin Derivatives: O-Acetyl-(4R)-4-(E-2-butyl)-4,N-dimethyl-L-threonyl-cyclosporin A and O-Acetyl-(4R)-4-[E-2-(4-bromobutyl)]-4,N-dimethyl-L-threonyl-cyclosporin A
Creators:
Kratochvíl, Bohumil
Jegorov, Alexandr
Pakhomova, Svetlana
Hušák, Michal
Bulej, Petr
Cvak, Ladislav
Sedmera, Petr
Havlíček, Vladimír
Uncontrolled Keywords:Cyclic peptides, X-Ray diffraction, Immunosupressants, Crystal structure determination, Cyclosporins, NMR spectroscopy
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:64
Number:1
Page Range:pp. 89-98
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19990089UNSPECIFIED
ID Code:1458
Item Type:Article
Deposited On:06 Feb 2009 17:09
Last Modified:06 Feb 2009 16:09

Citation

Kratochvíl, Bohumil; Jegorov, Alexandr; Pakhomova, Svetlana; Hušák, Michal; Bulej, Petr; Cvak, Ladislav; Sedmera, Petr; Havlíček, Vladimír (1999) Crystal Structures of Cyclosporin Derivatives: O-Acetyl-(4R)-4-(E-2-butyl)-4,N-dimethyl-L-threonyl-cyclosporin A and O-Acetyl-(4R)-4-[E-2-(4-bromobutyl)]-4,N-dimethyl-L-threonyl-cyclosporin A. Collection of Czechoslovak Chemical Communications, 64 (1). pp. 89-98. ISSN 0010-0765

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