Microbial hydroxylation of (Z)-2-benzylidene-1-azabicyclo[2.2.2]octan-3-one

Wong, John W.; Burns, Michael P.

doi:10.1016/s0957-4166(99)00471-1

Cited by 5 publications

(4 citation statements)

References 20 publications

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“…21-4. Moreover, we assigned Streptomyces noursei to A41733 and Streptomyces mirabilis to ATCC31561, which were previously Streptomyces albulus [26] and Streptomyces diastatochromogenes [27] , respectively. The closest 16S homologs to A41733 and ATCC31561 were Streptomyces noursei ATCC 11455 at 99.9% similarity and Streptomyces sp.…”

Section: Resultsmentioning

confidence: 99%

“…Put together, these analyses suggest that ATCC21481 is a potential new Streptomyces species within the known Genbank collection. GTDB-Tk based taxonomy (11) (Table 1) was also used to reassign Streptomyces noursei to A41733 and Streptomyces mirabilis to ATCC31561, which were previously Streptomyces albulus (27) and Streptomyces diastatochromogenes (28), respectively. The closest 16S homologs to A41733 and ATCC31561 were Streptomyces noursei ATCC 11455 at 99.9% similarity and Streptomyces sp.…”

Section: Resultsmentioning

confidence: 99%

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Cost-effective hybrid long-short read assembly delineates alternative GC-richStreptomyceschassis for natural product discovery

Heng¹,

Tan²,

Tay

et al. 2022

Preprint

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With the advent of rapid automated in silico identification of biosynthetic gene clusters (BGCs), genomics presents vast opportunities to accelerate natural product (NP) discovery. However, prolific NP producers, Streptomyces, are exceptionally GC-rich (>80%) and highly repetitive within BGCs. These pose challenges in sequencing and high-quality genome assembly which are currently circumvented via intensive sequencing. Here, we outline a more cost-effective workflow using multiplex Illumina and Oxford Nanopore sequencing with hybrid long-short read assembly algorithms to generate high quality genomes. Our protocol involves subjecting long read derived assemblies to up to 4 rounds of polishing with short reads to yield accurate BGC predictions. We successfully sequenced and assembled 8 GC-rich Streptomyces genomes whose lengths range from 7.1 to 12.1 Mb at an average N50 of 5.9 Mb. Taxonomic analysis revealed previous misrepresentation among these strains and allowed us to propose a potentially new species, Streptomyces sydneybrenneri. Further comprehensive characterization of their biosynthetic, pan-genomic and antibiotic resistance features especially for molecules derived from type I polyketide synthase (PKS) BGCs reflected their potential as NP chassis. Thus, the genome assemblies and insights presented here are envisioned to serve as gateway for the scientific community to expand their avenues in NP discovery.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Cost-effective hybrid long-short read assembly delineates alternative GC-richStreptomyceschassis for natural product discovery

Heng¹,

Tan²,

Tay

et al. 2022

Preprint

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show abstract

“…Biotransformation using Cunninghamella echinulata gave the same quantity of the alcohol (30% ee) and a slightly smaller quantity of a dihydroxylated derivative. 202 Botrytis cinerea has been shown to hydroxylate the antifungal ginsenol 99 at the 8-and 9-positions primarily. 203 2-Substituted indanes may be oxidized stereoselectively in the benzylic position(s) using toluene dioxygenases.…”

Section: Hydroxylation Reactionsmentioning

confidence: 99%

Preparative biotransformations

Roberts¹

2001

J. Chem. Soc., Perkin Trans. 1

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“…The only known procedure for functionalization at other sites in these α,β-unsaturated quinuclidines is hydroxylation with enzymes. [8] Alternative methods to prepare quinuclidines involve cyclizations of 4-substituted piperidines using the ring nitrogen atom as a nucleophile. [9] This strategy has been used for the total synthesis of cinchona alkaloids [9a-9d] and their derivatives.…”

Section: Introductionmentioning

confidence: 99%