Isolation of New Thiopeptide Berninamycin E from Streptomyces atroolivaceus

Abstract

Thiopeptide antibiotic, berninamycins A, was originally isolated from Streptomyces bernensis. In this report, new berninamycin analogue named berninamycin E was isolated using several procedures using column chromatography from acetone extract of S. atroolivaceus NBRC 12741. High resolution ESI-MS spectrum data determined the molecular fomula of berninamycin E as C51H53N15O15S. The structure of berninamycin E was determined using NMR and MS spectra.

Cytochromes P450 Associated with the Biosyntheses of Ribosomally Synthesized and Post-translationally Modified Peptides

“…In total 11 berninamycins have been isolated from a number of Streptomyces , 8 of which encompass a β-OHVal7 residue (berninamycins A, C, D, E, G, H, I, K, Figure ). − Moreover, a congener bearing two hydroxylations at Val7 was determined by MS/MS fragmentation studies, albeit in a trace amount of yield . Analysis of the berninamycin BGC identifies a P450 gene berH that is presumed for the hydroxylation at Val7 after scaffold macrocyclization .…”

α,β-Dehydroamino acids in naturally occurring peptides

“…The thiostrepton family of compounds 60 (Dutcher and Vandeputte 1955 ; Anderson et al 1970 ; Bond et al 2001 ; Nishimura et al 1959 ; Mori et al 2007 ; Tori et al 1981 ; Miyairi et al 1970 ; Hensens and Albers-Schönberg 1983 , 1978 ; Puar et al 1981 ) and closely related Sch 40832 61 (Puar et al 1998 ) contain the thiazoline-(Z)-dehydrobutyrine residue, in which the heterocyclic ring is not fully dehydrated. Furthermore, oxazole- and 5-methyl-oxazole-dehydroamino acids such as oxazole-dehydroalanine, 5-methyl-oxazole-dehydroalanine, oxazole-dehydrobutyrine, 5-methyl-oxazole-dehydrobutyrine, oxazole-dehydrohomobutyrine, 5-methyl-oxazole-dehydrohomobutyrine, oxazole-dehydroleucine, and 5-methyl-oxazole-dehydrohomoserine were found in geninthiocin 62 (Yun et al 1994a , b , c ), berninamycins (Liesch and Rinehart 1977 ; Abe et al 1988 ; Kodani and Ninomiya 2013 ), sulfomycins 63 (Egawa et al 1969 ; Kohno et al 1996 ; Vijaya Kumar et al 1999 ), promoinducin (Yun and Seto 1995 ), thiotipin (Yun et al 1994a , b , c ), A10255 64 (Boeck et al 1992 ; Debono et al 1992 ; Favret et al 1992 ), tioaxamycin (Yun et al 1994a , b , c ), radamycin (Castro Rodríguez et al 2002 ), and TP-1161 (Engelhardt et al 2010 ). Oxazole-dehydroalanine and oxazole-dehydrobutyrine were also found, respectively, in mechercharmycin A 65 (IB-01211) (Kanoh et al 2005 ; Hernández et al 2007a , b ) [226–228] and urukthapelstatin A (Matsuo et al 2007 ), a new class of thiopeptides of antitumour activity, which does not have six-membered heterocyclic moiety.…”