Volume 8, Issue 6, Pages (June 2001)

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Volume 8, Issue 6, Pages 569-581 (June 2001) Biosynthesis of the orthosomycin antibiotic avilamycin A: deductions from the molecular analysis of the avi biosynthetic gene cluster of Streptomyces viridochromogenes Tü57 and production of new antibiotics G Weitnauer, A Mühlenweg, A Trefzer, D Hoffmeister, R.D Süßmuth, G Jung, K Welzel, A Vente, U Girreser, A Bechthold Chemistry & Biology Volume 8, Issue 6, Pages 569-581 (June 2001) DOI: 10.1016/S1074-5521(01)00040-0

Fig. 1 Structure of avilamycin A, avilamycin C, gavibamycin A1, gavibamycin A3, gavibamycin B1 and gavibamycin B3. (A) Dichloroisoeverninic acid, (B, C) D-olivoses, (D) 2-deoxy-D-evalose, (E) 4-O-methyl-D-fucose, (F) 2,6-di-O-methyl-D-mannose, (G) 2-O-isobutyryl-L-lyxose, (H) methyleurekanate. Orthoester linkages and one methylene bridge are marked by arrows. Chemistry & Biology 2001 8, 569-581DOI: (10.1016/S1074-5521(01)00040-0)

Fig. 2 Genetic organization of the avilamycin biosynthetic gene cluster. Genes, belonging to the cluster, are indicated as dark arrows orientated in the direction of transcription. Genes, probably located outside the cluster, are shown as light arrows (B, BamHI). Chemistry & Biology 2001 8, 569-581DOI: (10.1016/S1074-5521(01)00040-0)

Fig. 3 Isotopic patterns of the main new derivatives produced by mutant S. viridochromogenes GW4. (A) Gavibamycin A1, (B) gavibamycin A3 and S. viridochromogenes GW4-AM1, (C) gavibamycin B1, (D) gavibamycin B3. Chemistry & Biology 2001 8, 569-581DOI: (10.1016/S1074-5521(01)00040-0)

Fig. 4 Reaction scheme for the treatment of avilamycin derivatives and gavibamycin derivatives for GC-MS analysis. Chemistry & Biology 2001 8, 569-581DOI: (10.1016/S1074-5521(01)00040-0)

Fig. 5 EI mass spectrum of the D-olivosyl ester of dichloro-di-O-ethyl-orsellinic acid. Chemistry & Biology 2001 8, 569-581DOI: (10.1016/S1074-5521(01)00040-0)

Fig. 6 Proposed biosynthetic pathway of avilamycin A. Chemistry & Biology 2001 8, 569-581DOI: (10.1016/S1074-5521(01)00040-0)