ChemInform Abstract: Structure of Sch 218157, a Cyclodepsipeptide with Neurokinin Activity.

Chu, Min; Chan, T. M.; Das, Pranab Jyoti; Mierzwa, Ronald; Patel, Mahesh; Puar, M. S.

doi:10.1002/chin.200048208

Cited by 3 publications

(5 citation statements)

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“…382 As noted previously, Cys residues within enzymes are known to catalyze a number of biological reactions, but an enzymatic, cysteine-mediated RC reaction had not yet been identified. However, we wondered if a cysteine-dependent enzyme might be capable of mediating the ring contraction of 8.19 to 8.20 en route to 8.21.…”

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confidence: 94%

Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms

et al. 2020

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Low molecular weight synthetic peptides have been demonstrated to be effective catalysts for an increasingly wide array of asymmetric transformations. In many cases, these peptide-based catalysts have enabled novel multifunctional substrate activation modes and unprecedented selectivity manifolds. These features, along with their ease of preparation, modular and tunable structures, and often biomimetic attributes make peptides well-suited as chiral catalysts, and of broad interest. Many examples of peptide-catalyzed asymmetric reactions have appeared in the literature since the last survey of this broad field in Chemical Reviews (Chem. Rev. 2007, 107, 5759-5812). The overarching goal of this new review is to provide a comprehensive account of the numerous advances in the field. As a corollary to this goal, we survey the many different types of catalytic reactions, ranging from acylation to C-C bond formation, in which peptides been successfully employed. In so doing, we devote significant discussion to the structural and mechanistic aspects of these reactions that are perhaps specific to peptide-based catalysts and their interactions with substrates and/or reagents.

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confidence: 94%

Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms

et al. 2020

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“…BA-12233 (FERM P-10492)], 44 Sch-538415 (produced by Streptomyces sp. ), 45,46 pseudonocardians A-C (derived from the deep-sea actinomycete Pseudonocardia sp. SCSIO 01299), 43 diazaquinomycin A [also known as antibiotic OM 704A and NSC 626554; derived from Streptomyces sp.…”

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confidence: 99%

Structure Determination, Functional Characterization, and Biosynthetic Implications of Nybomycin Metabolites from a Mining Reclamation Site-Associated Streptomyces

et al. 2019

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“…9 Transcription profiling experiments and the central quinone substructure of DAQs suggest that cell damage in M. tuberculosis may be caused by extensive redox chemistry. 9 DAQs show structural similarity to nybomycin (10), 10, 11 deoxynybomycin (11), 10,11 SCH 538415 (12), 12 and deoxynyboquinone (13) (Figure 1). 10,13 Nybomycin was originally isolated from the terrestrial Streptomyces sp.…”

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confidence: 99%

“…15 Deoxynybomycin (11), originally described as a degradation product of 10, 10 was later found to be produced by a soil Streptomyces hyalinum strain and to have more potent activity than 10. 16,17 SCH 538415 (12) was isolated in 2003 from an unidentified bacterial microbe during a mechanism-based drug discovery campaign aimed at identifying inhibitors of bacterial acyl carrier protein synthetase, 12 and again three years later from a riverbank soil-derived Streptomyces sp. 18 It was reported to possess anticancer and moderate antibacterial activity.…”

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confidence: 99%

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Diazaquinomycin Biosynthetic Gene Clusters from Marine and Freshwater Actinomycetes

et al. 2019

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Tuberculosis is an infectious disease of global concern. Members of the diazaquinomycin (DAQ) class of natural products have shown potent and selective activity against drug-resistant Mycobacterium tuberculosis. However, poor solubility has prevented further development of this compound class. Understanding DAQ biosynthesis may provide a viable route for the generation of derivatives with improved properties. We have sequenced the genomes of two actinomycete bacteria that produce distinct DAQ derivatives. While software tools for automated biosynthetic gene cluster (BGC) prediction failed to detect DAQ BGCs, comparative genomics using MAUVE alignment led to the identification of putative BGCs in the marine Streptomyces sp. F001 and in the freshwater Micromonospora sp. B006. Deletion of the identified daq BGC in strain B006 using CRISPR-Cas9 genome editing abolished DAQ production, providing experimental evidence for BGC assignment. A complete model for DAQ biosynthesis is proposed based on the genes identified. Insufficient knowledge of natural product biosynthesis is one of the major challenges of productive, genome mining approaches. The results reported here fill a gap in knowledge regarding the genetic basis for the biosynthesis of DAQ antibiotics. Moreover, identification of the daq BGC shall enable future generations of improved derivatives using biosynthetic methods.

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ChemInform Abstract: Structure of Sch 218157, a Cyclodepsipeptide with Neurokinin Activity.

Abstract: Structure of Sch 218157, a Cyclodepsipeptide with NeurokininActivity.--(CHU, M.; CHAN, T. M.; DAS, P.; MIERZWA, R.; PATEL, M.; PUAR, M. S.; J. Antibiot. 53 (2000) 7, 736-738; Schering-Plough Res. Inst., Kenilworth, NJ 07033, USA; EN)

Cited by 3 publications

References 1 publication

Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms

Asymmetric Catalysis Mediated by Synthetic Peptides, Version 2.0: Expansion of Scope and Mechanisms

Structure Determination, Functional Characterization, and Biosynthetic Implications of Nybomycin Metabolites from a Mining Reclamation Site-Associated Streptomyces

Diazaquinomycin Biosynthetic Gene Clusters from Marine and Freshwater Actinomycetes

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