Tetrahedron

Isolation of an isomer of FK-506 from fermentation of Streptomyces tsukubaensis and its chemical synthesis from FK-506

MA Grassberger, T Fehr, A Horvath, G Schulz

Index: Grassberger, Maximilian A.; Fehr, Theodor; Horvath, Amarylla; Schulz, Gerhard Tetrahedron, 1992 ,  vol. 48,  # 3  p. 413 - 430

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Citation Number: 15

Abstract

From the fermentation broth of Streptomyces tsukubaensis 9993 an isomer 2a of the immunosuppressant FK-506 1a was isolated as a minor metabolite. From NMR-and FAB-MS data follows that in 2a the size of the macrocycle is reduced by two carbon atoms due to a shift of the lactone-acyl from 0–26 to 0–24. The compound was synthesized from FK-506 and proved to be identical with the natural product 2a.