Dissecting Glycosylation Steps in Lobophorin Biosynthesis Implies an Iterative Glycosyltransferase

Li, Sumei; Xiao, Jianru; Zhu, Yiguang; Zhang, Guangtao; Yang, Chunfang; Zhang, Haibo; Ma, Liang

doi:10.1021/ol400342e

Cited by 47 publications

(72 citation statements)

References 31 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The gene cluster involved in biosynthesis of lobophorin was the first type I PKS gene cluster identified from the deep sea derived Streptomyces . Three glycosyltransferases (GTs) LobG1-LobG3 genes-inactivation mutants yielded five different glycosylated metabolites, and the result suggested that LobG3 as an iterative GT to attach two L-digitoxoses (Li et al, 2013). Desotamides B, C and D together with a known desotamide A were obtained from deep sea derived Streptomyces scopuliridis SCSIO ZJ46, recovered from sediment sample collected at a depth of 3,536 m in the South China Sea (Song et al, 2014).…”

Section: Biosynthesis Pathways For Deep Sea Streptomycetes Natural Prmentioning

confidence: 99%

Deep Sea Actinomycetes and Their Secondary Metabolites

et al. 2017

View full text Add to dashboard Cite

Deep sea is a unique and extreme environment. It is a hot spot for hunting marine actinomycetes resources and secondary metabolites. The novel deep sea actinomycete species reported from 2006 to 2016 including 21 species under 13 genera with the maximum number from Microbacterium, followed by Dermacoccus, Streptomyces and Verrucosispora, and one novel species for the other 9 genera. Eight genera of actinomycetes were reported to produce secondary metabolites, among which Streptomyces is the richest producer. Most of the compounds produced by the deep sea actinomycetes presented antimicrobial and anti-cancer cell activities. Gene clusters related to biosynthesis of desotamide, heronamide, and lobophorin have been identified from the deep sea derived Streptomyces.

show abstract

Section: Biosynthesis Pathways For Deep Sea Streptomycetes Natural Prmentioning

confidence: 99%

Deep Sea Actinomycetes and Their Secondary Metabolites

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Both the cyclohexene and trans - decalin rings have been proposed to be assembled via Diels-Alder cycloaddition reactions. [321] Although the gene clusters responsible for the biosynthesis of chlorothricin, [322] kijanimicin, [323] tetrocarcin A, [324] abyssomicin C, [325] lobophorin, [326] , quartromicin, [327] and other spirotetronates had been identified, no gene could be assigned to encode a putative “Diels-Alderase” in each cluster. A breakthrough was made when Hashimoto et al discovered a small protein, VstJ, which catalyzes the stereoselective [4+2] cycloaddition to form the spirotetronate structure in versipelostatin ( 321 ).…”

Section: Rearrangementmentioning

confidence: 99%

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

2017

View full text Add to dashboard Cite

Chemical reactions that are named in honor of their true or at least perceived discoverers are known as “name reactions”. This review is a collection of biological representatives of named chemical reactions. Emphasis is placed on reaction types and catalytic mechanisms that showcase both the chemical diversity in natural product biosynthesis as well as the parallels with synthetic organic chemistry. An attempt has been made to describe the enzymatic mechanisms of catalysis within the context of their synthetic counterparts whenever possible and to discuss the mechanistic hypotheses for those reactions that are presently active areas of investigation. This review has been categorized by reaction type, e.g., condensation, nucleophilic addition, reduction and oxidation, substitution, carboxylation, radical-mediated, and rearrangements, which are subdivided by named reactions.

show abstract

“…Recently, biosynthetic gene clusters for lobophorins and its polyketide relatives have been described, providing a platform for engineering to produce desired derivatives. 32–34 Interestingly, elucidation of the glycosylation steps shows definitively that compounds similar to 1 are precursors to other compounds in the series.…”

Section: Discussionmentioning

confidence: 99%

Structure and activity of lobophorins from a turrid mollusk-associated Streptomyces sp

et al. 2013

View full text Add to dashboard Cite

A novel lumun-lumun sampling methodology was used to obtain a large diversity of micromollusks, including the new species Lienardia totopotens. In turn, from L. totopotens we cultivated a Streptomyces sp. strain that contained new and known spirotetronate polyketides, lobophorins (1–5). The structures were elucidated using spectroscopy, and the compounds were evaluated for cytotoxicity to human cells and activity against Mycobacterium tuberculosis. A structure-activity relationship was discerned, wherein the lack of digitoxose in 1 led to lack of both cytotoxic and antibacterial activity. For compounds 2–5 both activities were in the low μM to mid nM range. Although this likely precludes their direct application in tuberculosis therapy due to possible poor therapeutic index, very slight changes in structure led to widely varying antibacterial:cytotoxicity ratios, providing a possible basis to synthesize more selective derivatives.

show abstract

Dissecting Glycosylation Steps in Lobophorin Biosynthesis Implies an Iterative Glycosyltransferase

Cited by 47 publications

References 31 publications

Deep Sea Actinomycetes and Their Secondary Metabolites

Deep Sea Actinomycetes and Their Secondary Metabolites

The Enzymology of Organic Transformations: A Survey of Name Reactions in Biological Systems

Structure and activity of lobophorins from a turrid mollusk-associated Streptomyces sp

Contact Info

Product

Resources

About