Synthetic studies towards bottromycin
نویسندگان
چکیده
Thio-Ugi reactions are described as an excellent synthetic tool for the synthesis of sterically highly hindered endothiopeptides. S-Methylation and subsequent amidine formation can be carried out in an inter- as well as in an intramolecular fashion. The intramolecular approach allows the synthesis of the bottromycin ring system in a straightforward manner.
منابع مشابه
Mechanism of protein synthesis inhibition by bottromycin A2: studies with puromycin.
Bottromycin A2 inhibits polylysine synthesis with poly A at low concentrations of E. coli ribosomes. Peptide release by puromycin from ribosomes was significantly inhibited by blasticidin S, chloramphenicol and thiophenicol, but not by bottromycin A2 in the absence of GTPand G factor. Puromycindependent release of peptide from ribosomes was stimulated by the presence of GTP and G factor; it was...
متن کاملDissecting Bottromycin Biosynthesis Using Comparative Untargeted Metabolomics
Bottromycin A2 is a structurally unique ribosomally synthesized and post-translationally modified peptide (RiPP) that possesses potent antibacterial activity towards multidrug-resistant bacteria. The structural novelty of bottromycin stems from its unprecedented macrocyclic amidine and rare β-methylated amino acid residues. The N-terminus of a precursor peptide (BtmD) is converted into bottromy...
متن کاملMode of action of bottromycin A2. Release of aminoacyl- or peptidyl-tRNA from ribosomes.
Bottromycin A2 inhibited MS2 phage RNA-dependent protein synthesis as well as polyuridylic acid-(poly(U))- or polyadenylic acid (poly(A))-dependent polypeptide synthesis. When the ribosomal complex with N-acetyl-[14C]phenylalanyl-tRNA (N-acetyl-[14C]Phe-tRNA) at the A site was subjected to bottromycin A2, the release of N-acetyl-[14C]Phe-tRNA was observed while no release of N-acetyl-[14C]Phe-t...
متن کاملDraft Genome Sequence of Streptomyces bottropensis ATCC 25435, a Bottromycin-Producing Actinomycete
A series of bottromycin antibiotics have been isolated and identified from Streptomyces bottropensis strain ATCC 25435. Here, a draft genome sequence of S. bottropensis ATCC 25435 is presented. The genome carries an intact biosynthetic gene cluster for bottromycin antibiotics, which provides insight into the combinatorial biosynthesis of bottromycin antibiotics.
متن کاملStudies on bottromycins. I. 1H and 13C NMR assignments of bottromycin A2, the main component of the complex.
Bottromycins were first isolated from Streptomyces bottropensis by Waisvisz et al.1} and are especially active against Gram-positive bacteria and Mycoplasma1"3^.The complete structure of bottromycin A2 (1), the main active component of the complex, was first proposed by Nakamura et al. in 1966 as a linear peptide4'5), but the structure was revised in 1976 by Takahashi et al.6) to a partly cycli...
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عنوان ژورنال:
دوره 8 شماره
صفحات -
تاریخ انتشار 2012