Fk-900520 enzymatic and/or microbial methylation products

C - Chemistry – Metallurgy – 12 – P

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C12P 17/18 (2006.01) C07D 307/20 (2006.01) C07D 309/10 (2006.01) C07H 19/01 (2006.01) C12N 9/10 (2006.01) C12P 19/26 (2006.01)

Patent

CA 2071066

F1 54/RJN26 - i - 18445 TITLE OF THE INVENTION NEW FK-900520 ENZYMATIC AND/OR MICROBIAL METHYLATION PRODUCTS ABSTRACT OF THE DISCLOSURE Described is a new enzyme, 31-O-desmethyl- immunomycin O-methyltransferase (DIMT) which can specifically and preferentially methylate the C-31 hydroxy group in immunomycin type molecules, also designated FK520 and FR-900520 by Fujisawa. The enzyme can be extracted out of the microorganism Streptomyces hydroscopicus var. ascomyceticus, (Merck Culture Collection No. MA 6678) ATCC No. 55087. Employing the enzyme in its active form, supplemented with Mg +2 ion, in the presence of the methyl donor, S-adenosyl methionine (SAM), a new FK520 (FR-900520) derivative has been prepared: 15-desmethyl FR-900520, made from 15,31-bisdesmethyl FK-900520. This new macrolide can act as an anta- gonist at moderately low dosages and reverse the F1 54/RJN26 - ii - 18445 immunosuppressant action of FK-506, and can be used diagnostically as a tool to determine the presence of FK-506 macrolide type immunosuppressants in natural product broths, distinguishing such immunosuppressants from other chemical families such as the cyclosporins. Also, it can act as antagonist at higher dosages and much lower dosages and is useful in preventing human host rejection of foreign organ transplants, e.g. bone marrow, liver, lung, kidney and heart transplants.

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