Structure of awamycin, a novel antitumor ansamycin antibiotic.

Catellatolactams A–C, Plant Growth-Promoting Ansamacrolactams from a Rare Actinomycete of the Genus Catellatospora

“…The 1,3,5-trisubstituted benzene units in 1 and 3 and the corresponding aromatic moiety in 2 are presumably derived from 3-amino-5-hydroxybenzoic acid (AHBA). , AHBA is known to be a biosynthetic starter for polyketides such as ansamycin-class secondary metabolites . Based on the structures, a presumable biosynthetic pathway of 1 – 3 is outlined in Scheme .…”

Methanethiol as a catabolite of methionine provides methylthio- group for chemical formation of 19-S-methylgeldanamycin and 17,19-dimethylthioherbimycin A

“…An examination of natural ansamycins reveals quite a few compounds with methylthio-group (such as trierixin, quinotrierixin, awamycin and 3-methylthiorifamycin SV, Figure 1) linking to an aromatic carbon of the molecules. [6][7][8][9] Besides, urdamycin E as an angucycline antibiotic contains also a methylthio-group ( Figure 1). 10 Among these compounds, urdamycin E and 3-methylthiorifamycin SV were known to be closely related to L-methionine (Met) for their production.…”

A pair of sulfur-containing geldanamycin analogs, 19-S-methylgeldanamycin and 4,5-dihydro- 19-S-methylgeldanamycin, from Streptomyces hygroscopicus 17997

“…Some hindered amines could also undergo addition reaction in vitro at C19-of GDM nonenzymatically. 7,8 Several sulfur-containing ansamycins, such as thiazinotrienomycin, trierixin, 3-methylthiorifamycin SV and thiazorifamycins, naphthomycins I and J, and awamycin [23][24][25][26][27][28] had been isolated from Micromonospora sp. or Streptomyces sp.…”