Genome Sequence of Marine-Derived Streptomyces sp. Strain F001, a Producer of Akashin A and Diazaquinomycins

Abstract

We report the 9.7-Mb genome sequence of Streptomyces sp. strain F001, isolated from a marine sediment sample from Raja Ampat, Indonesia.

Total synthesis of the chlorinated indigo-N-glycosides akashin A, B and C

“…The chemical shifts of akashin A (1) containing a primary amino group were less consistent with the reported data of the 1 H-spectra ( max = -0.5 ppm for H-4'' of 1) and the 13 C-spectra ( max = +4.2 ppm for C-5'' of 1). In contrast, for akashin C (3) with a secondary amine the comparison of the NMR data was quite satisfactory for protons ( 1 H:  max = -0.15 ppm for H-3'' of 3) and 13 C ( = -1.7 + 0.4 ppm for all signals of 3). The 1 H-NMR shifts of the sugar part of 1 were significantly affected by adding some hydrochloric acid to the NMR sample of synthetic 1.…”

“…11 The assignment of the resonances was in line with the data reported previously. Only minor differences were found for the neutral akashin B (2) where the position of the reported 1 H-signals were deviating only up to ( max ) 0.06 ppm and the 13 C signals up to 0.7 ppm in DMSO-D6. The chemical shifts of akashin A (1) containing a primary amino group were less consistent with the reported data of the 1 H-spectra ( max = -0.5 ppm for H-4'' of 1) and the 13 C-spectra ( max = +4.2 ppm for C-5'' of 1).…”

“…Only minor differences were found for the neutral akashin B (2) where the position of the reported 1 H-signals were deviating only up to ( max ) 0.06 ppm and the 13 C signals up to 0.7 ppm in DMSO-D6. The chemical shifts of akashin A (1) containing a primary amino group were less consistent with the reported data of the 1 H-spectra ( max = -0.5 ppm for H-4'' of 1) and the 13 C-spectra ( max = +4.2 ppm for C-5'' of 1). In contrast, for akashin C (3) with a secondary amine the comparison of the NMR data was quite satisfactory for protons ( 1 H:  max = -0.15 ppm for H-3'' of 3) and 13 C ( = -1.7 + 0.4 ppm for all signals of 3).…”

“…The O-glycoside was further supported by the 13 The 1 H-NMR spectra of 20b also indicated an O-glycoside ( 13 C-NMR signal at 99.3 ppm for C-1''), however, with a small anomeric coupling constant (J1'',2'' = 3.4 Hz for H-1'') corresponding to an -glycoside. We first assumed an orthoester but in the 13 C-NMR spectrum of 20b the carbonyl groups of both benzoates were present. Furthermore, the chemical shift of H-2 in 20b was very similar to 20a (20a H-2": 5.38 ppm: 20b H-2": 5,35 ppm) thus ruling out an orthoester structure for 20b.…”

“…15 Additionally, also the enantiomer L-viosamine is part of natural products and antibiotics like amicetin, 16 norplicacetin, 17 tallysomicin 18 and the family of calicheamicins. 19 Several approaches were developed for the synthesis of N-glycosylated indole derivatives comprising the indole-indolin-method by Preobrazhenskaya [13] and the direct acid-mediated glycosylation of substituted indoles [14] . For more than 100 years the preparation of synthetic indigo is known by dimerization of indoxyl in the presence of oxygen [15] .…”