Application of centrifugal counter-current chromatography to the separation of macrolide antibiotic analogues: I. Selection of solvent systems based on solubility and partition coefficient investigations

作者: Weizheng Wang-Fan , Ernst Küsters , Olivier Lohse , Ching-Pong Mak , Ying Wang

DOI: 10.1016/S0021-9673(99)01012-2

关键词: Partition coefficientSolubilityCountercurrent chromatographySelectivityMethanolChemistryAscomycinSolventTernary operationChromatography

摘要: As the first part of our studies on counter-current chromatography, methodology for selecting suitable solvent systems was established based detailed investigations solubility and partition coefficients (log K) macrolide antibiotic analogues. The two important macrolides, ascomycin FK-506, measured in a series common solvents, where their polarities were ranked with dielectric constants. macrolides compared various binary, ternary, quaternary systems. Hexane-tert.-butyl methyl ether-methanol-water system selected log K solutes hydrogen-bonding properties solvents. In further optimisation composition proportions multicomponent system, hexane-tert.-butyl (1:3:6:5) showed best selectivity by giving most prominent difference coefficient (delta between FK-506. With this baseline preparative separation these very closely related 23-membered antibiotics successfully achieved employing newly introduced Quattro chromatograph.

参考文章(23)
Y Kawase, S Sawada, F Takaku, G Suzuki, Novel immunosuppressive agent, FK506. In vitro effects on the cloned T cell activation Journal of Immunology. ,vol. 139, pp. 1797- 1803 ,(1987)
A. Marston, K. Hostettmann, Counter-current chromatography as a preparative tool —applications and perspectives Journal of Chromatography A. ,vol. 658, pp. 315- 341 ,(1994) , 10.1016/0021-9673(94)80023-5
Hirokazu Tanaka, Akio Kuroda, Hiroshi Marusawa, Hiroshi Hatanaka, Toru Kino, Toshio Goto, Masashi Hashimoto, Toru Taga, Structure of FK506, a novel immunosuppressant isolated from Streptomyces Journal of the American Chemical Society. ,vol. 109, pp. 5031- 5033 ,(1987) , 10.1021/JA00250A050
Amos B. Smith, Karl J. Hale, Leif M. Laakso, Kwunmin Chen, Antoni Riéra, FK-506 synthetic studies. 3. An efficient asymmetric synthesis of the C(24)–C(34) fragment of FK-506, FR-900520, and FR-900523 Tetrahedron Letters. ,vol. 30, pp. 6963- 6966 ,(1989) , 10.1016/S0040-4039(01)93398-2
MAKOTO UBUKATA, NORIO SHIRAISHI, KIMIE KOBINATA, TAKUJI KUDO, ISAMU YAMAGUCHI, HIROYUKI OSADA, YIN-CHU SHEN, KIYOSHI ISONO, RS-22A, B and C: new macrolide antibiotics from Streptomyces violaceusniger. I. Taxonomy, fermentation, isolation and biological activities. The Journal of Antibiotics. ,vol. 48, pp. 289- 292 ,(1995) , 10.7164/ANTIBIOTICS.48.289
Weizheng Fan, Ruey Shiuan Tsai, Nabil El Tayar, Pierre Alain Carrupt, Bernard Testa, Soluble-water interactions in the organic phase of a biphasic system. 2. Effects of organic phase and temperature on the "water-dragging" effect The Journal of Physical Chemistry. ,vol. 98, pp. 329- 333 ,(1994) , 10.1021/J100052A054
Matthew W. Harding, Andrzej Galat, David E. Uehling, Stuart L. Schreiber, A receptor for the immunosuppressant FK506 is a cis-trans peptidyl-prolyl isomerase. Nature. ,vol. 341, pp. 758- 760 ,(1989) , 10.1038/341758A0
Weizheng. Fan, Nabil. El Tayar, Bernard. Testa, Lemont B. Kier, Water-dragging effect : a new experimental hydration parameter related to hydrogen-bond-donor acidity The Journal of Physical Chemistry. ,vol. 94, pp. 4764- 4766 ,(1990) , 10.1021/J100375A003
HIROSHI HATANAKA, TOHRU KINO, SUSUMU MIYATA, NORIAKI INAMURA, AKIO KURODA, TOSHIO GOTO, HIROKAZU TANAKA, MASAKUNI OKUHARA, FR-900520 and FR-900523, novel immunosuppressants isolated from a Streptomyces. II. Fermentation, isolation and physico-chemical and biological characteristics. The Journal of Antibiotics. ,vol. 41, pp. 1592- 1601 ,(1988) , 10.7164/ANTIBIOTICS.41.1592
Randal H. Chen, Jill E. Hochlowski, James B. McAlpine, Ronald R. Rasmussen, Separation and purification of macrolides using the ito multi-layer horizontal coil planet centrifuge Journal of Liquid Chromatography & Related Technologies. ,vol. 11, pp. 191- 201 ,(1988) , 10.1080/01483919808068322