300 Chapter 9 Substrate Product Mcr。 organIs8m 19-hydroxysterols, estrone Nocardia restrictus ATCC 14887 3 hydroxy-19nor△35 Nocardia sp ATCC 19170 sterols Arthrobacter simplex IAM 166 Corynebacterum sp M 9 hydroxy-△4-steo lin, equilenin, estrone Mycobacterium sp 3-ht Corynebacterium simplex sterols 6B, 19-oxidostenone 6B, 19-oxido-4-androstene-3, Nocardia sp ATCC 19170 Mycobacteria 19-oxidosterols 5a-bromo-6B, 19- 5a-bromo-6B, 19-0xidoandros- Nocardia sp ATCC 19170 ne 3.17-dione 5a, 5a-cyclosterols 3a, 5a-cycloandrostane-17-one Mycobactenum ph a,5αcyco6β,19ox a-cyclo-6B, 19-oxido- sterol-3-oximes 4-androstene-3 17-dione (after hydrolysis) 4-hydroxycholestenone 3B-hydroxy-5a-androstane-4, Mycobactenum phle 4a-dihydroxy-5a-andro 25D-spirost-4-ene-3-one 1. 4-androstadiene-3.16-dione. Fusanum solani 20a-hydroxy-4-pregnene-3, 16- Verticillium theobromae a,11B, 20a-trihydroxy-5a- ponasterone A rubrosterone Fusanum lini9593 Table 9.1 The use of modified sterols to allow selective cleavage of the side chain(based Martin, CKA Sterols in Biotechnology Volume 6a Edited by Kieslich K 1984 Verlag Chemie 9.3.1 Use of modified sterols First, let us briefly examine the route of side chain degradation in micro-organisms. The pathway is illustrated in Figure 9.2.300 Chapter 9 Substrate Produd Mlcro-organlsm 1 9-hydroxysterols, 1 9-norsterols, 3-hydro~y-19-nor-A’~~~~- sterols 19-hydro~y-A~~~-steroIs, 9-hydro~y-l9-nor-A’~~*~~’- sterols Sp,lO-oxidostenones, 3p-acetoxyda-chloro(fluoro)- Sp, 19-oxidosterols 3p-acetoxy-5a-bromo-Gp, 1 9- Dxidosterols 5a,5a-cyclosterols 3a,5a-cyclo-6p, 1 O-oxido￾jterols sterol-3-oximes I-hydroxycholestenone masterone A estrone Nocardia restrictus ATCC 14887 Nocardia sp ATCC 191 70 Arthrobacter simplex I AM 166( Corynebacterium sp M ycobaderia Corynebacterium simplex Nocardia mbra Sp, 19-oxido-4-androstene-3, Nocardia sp ATCC 191 70 17dione Mycobacteria 5a-bromo-Gfi,19-oxidoandros- Nocardia sp ATCC 191 70 tane3,17dione 3s5a-cycloandrostane-17-one Mycobacterium phlei 3a,5a-cyclo-6p, 1 9-oxido-an- Arthrobacter spp drostane-17-0ne Corynebacteria 4-androstene-3,17-dione Mymbacterium sp (after hydrolysis) 38 hydroxy-5a-androstane-4, Mycobactenurn phlei 17dione 3a-hydroxy-5a-androstane-4, 17dionq 3p,4u4i hydroxy-5a-andro￾stane-17-One 1 ,4-androstadiene-3,1 Gdione, Fusarium solani 20a-hydroxy-4pregnene-3,16- Verticillium theobromae dione Stachylklium bicolor 3a,l1 p,20a-trihydroxy-5a￾pregnane-16-one rubrosterone Fusarium lini 9593 equilin, equilenin, estrone Mycobacterium sp Table 9.1 The use of modified sterols to allow selective cleavage of the side chain (based on Martin, CKA Sterols in Biotechnology Volume 6a Edited by Kieslich K 1984 Verlag Chemie, Wein heim). 9.3.1 Use of modified sterols First, let us briefly examine the mute of side chain degradation in micro-organisms. ’Ihe pathway is illustrated in Figure 92