Collect. Czech. Chem. Commun.
2000, 65, 1317-1328
https://doi.org/10.1135/cccc20001317
Synthesis and Crystal Structure Determination of Cyclosporin H
Alexandr Jegorova,*, Ladislav Cvakb, Aleš Husekb, Petr Šimekc, Anna Heydovác, Jan Ondráčekd, Svetlana Pakhomovad, Michal Hušákd,e, Bohumil Kratochvíld, Petr Sedmeraf and Vladimír Havlíčekf
a Galena a.s., Branišovská 31, 370 05 České Budějovice, Czech Republic
b Galena a.s., 747 70 Opava-Komárov, Czech Republic
c Institute of Entomology, Academy of Sciences of the Czech Republic, Branišovská 31, 370 05 České Budějovice, Czech Republic
d Department of Solid State Chemistry, Prague Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic
e Laboratory of Biomembranes, South Bohemian University, Branišovská 31, 370 05 České Budějovice, Czech Republic
f Institute of Microbiology, Academy of Sciences of the Czech Republic, Vídeňská 1083, 142 20 Prague 4, Czech Republic
Abstract
Acid-catalyzed degradation of cyclosporin A was studied in various solvents and products of reaction were monitored by HPLC. Identification of amino acids and their chirality were determined after hydrolysis and derivatization by GC-MS. Cyclosporin H was isolated as the principal product and its structure was determined by X-ray diffraction: Cyclosporin H- diethyl ether-water (1 : 0.5 : 1) crystallizes in the monoclinic space group I2 with a = 12.338(2) Å, b = 18.963(2) Å, c = 34.074(3) Å, β = 96.47(2)°, Z = 4, and V = 7 921.4(17) Å3.
Keywords: Cyclosporins; Conformation analysis; Crystal structure determination; X-Ray diffraction; Hydrolysis; Amino acids; Peptides; Racemization; Immunosuppressants.
References: 47 live references.
