Deciphering the Biosynthetic Origin of L-allo-Isoleucine.
Journal of the American Chemical Society 138(1):408 (2016)
The nonproteinogenic amino acid L-allo-isoleucine (L-allo-Ile) is featured in an assortment of life forms comprised of, but not limited to, bacteria, fungi, plants and mammalian systems including Homo sapiens. Despite its ubiquity and functional importance, the specific origins of this unique am...
Activation of a plasmid-situated type III PKS gene cluster by deletion of a wbl gene in deepsea-derived Streptomyces somaliensis SCSIO ZH66.
Microbial Cell Factories 15(1):116 (2016)
Actinomycete genome sequencing has disclosed a large number of cryptic secondary metabolite biosynthetic gene clusters. However, their unavailable or limited expression severely hampered the discovery of bioactive compounds. The whiB-like (wbl) regulatory genes play important roles in morphologi...
A new diketopiperazine derivative from a deep sea-derived Streptomyces sp. SCSIO 04496.
Natural Product Research 30(2):138 (2016)
A new diketopiperazine (DKP) derivative, (6R,3Z)-3-benzylidene-6-isobutyl-1-methyl piperazine-2,5-dione (1), as well as five known DKPs 2-6 was isolated from a deep sea-derived Streptomyces sp. SCSIO 04496. The structure of 1 was elucidated using a combination of 1D and 2D NMR, HR-ESI-MS and chi...
Minimum Information about a Biosynthetic Gene cluster.
Nature Chemical Biology 11(9):625 (2015)
Leinamycin E1 acting as an anticancer prodrug activated by reactive oxygen species.
PNAS 112(27):8278 (2015)
Leinamycin (LNM) is a potent antitumor antibiotic produced by Streptomyces atroolivaceus S-140, featuring an unusual 1,3-dioxo-1,2-dithiolane moiety that is spiro-fused to a thiazole-containing 18-membered lactam ring. Upon reductive activation in the presence of cellular thiols, LNM exerts its ...
Identification of the Biosynthetic Gene Cluster for the Anti-infective Desotamides and Production of a New Analogue in a Heterologous Host.
Journal of Natural Products 78(4):944 (2015)
The desotamides (DSAs) are potent antibacterial cyclohexapeptides produced by Streptomyces scopuliridis SCSIO ZJ46. We have identified the 39-kb dsa biosynthetic gene cluster by whole-genome scanning. Composed of 17 open reading frames, the cluster codes for four nonribosomal peptide synthetases...
Biosynthesis of the anti-infective marformycins featuring pre-NRPS assembly line N-formylation and O-methylation and post-assembly line C-hydroxylation chemistries.
Organic Letters 17(6):1509 (2015)
The biosynthetic gene cluster governing production of anti-infective marformycins was identified from deep sea-derived Streptomyces drozdowiczii SCSIO 10141. The putative mfn gene cluster (45 kb, 20 orfs) was found to encode six NRPSs and related proteins for cyclodepsipeptide core construction ...
Cytotoxic and antibacterial angucycline- and prodigiosin-analogues from the deep-sea derived Streptomyces sp. SCSIO 11594.
Marine Drugs 13(3):1304 (2015)
Two new C-glycoside angucyclines, marangucycline A (1) and marangucycline B (2), along with three known compounds, dehydroxyaquayamycin (3), undecylprodigiosin (4) and metacycloprodigiosin (5), have been identified as products of the deep-sea sediment strain Streptomyces sp. SCSIO 11594. New str...
Discovery of a new family of Dieckmann cyclases essential to tetramic acid and pyridone-based natural products biosynthesis.
Organic Letters 17(3):628 (2015)
Bioinformatic analyses indicate that TrdC, SlgL, LipX2, KirHI, and FacHI belong to a group of highly homologous proteins involved in biosynthesis of actinomycete-derived tirandamycin B, streptolydigin, α-lipomycin, kirromycin, and factumycin, respectively. However, assignment of their biosynthet...
Activation and enhancement of Fredericamycin A production in deepsea-derived Streptomyces somaliensis SCSIO ZH66 by using ribosome engineering and response surface methodology.
Microbial Cell Factories 14:64 (2015)
Marine microorganisms are an important source of new drug leads. However, the discovery and sustainable production of these compounds are often hampered due to the unavailable expression of cryptic biosynthetic gene clusters or limited titer. Ribosome engineering and response surface methodology...
Comparative characterization of the lactimidomycin and iso-migrastatin biosynthetic machineries revealing unusual features for acyltransferase-less type I polyketide synthases and providing an opportunity to engineer new analogues.
Biochemistry (Washington) 53(49):7854 (2014)
Lactimidomycin (LTM, 1) and iso-migrastatin (iso-MGS, 2) belong to the glutarimide-containing polyketide family of natural products. We previously cloned and characterized the mgs biosynthetic gene cluster from Streptomyces platensis NRRL 18993. The iso-MGS biosynthetic machinery featured an acy...
New anti-infective cycloheptadepsipeptide congeners and absolute stereochemistry from the deep sea-derived Streptomyces drozdowiczii SCSIO 10141
Tetrahedron 70(42):7795 (2014)
Six cycloheptadepsipeptides, marformycins A–F (1–6), featuring a unique N-terminally formylated side chain and five non-proteinogenic amino acid residues, were isolated from the deep Sea-derived Streptomyces drozdowiczii SCSIO 10141. The previously unsolved absolute stereochemistry of ...
Expression, crystallization and preliminary X-ray analysis of McbB, a multifunctional enzyme involved in β-carboline skeleton biosynthesis.
Acta crystallographica. Section F, Structural b... 70(Pt 10):1402 (2014)
β-Carboline alkaloids (βCs), with tricyclic pyrido[3,4-b]indole rings, have important pharmacological and therapeutic value. In the biosynthesis of βCs, the Pictet-Spengler (PS) cyclization reaction is responsible for the formation of ring structures. McbB is one of a few enzymes that are known ...
Cyclic Hexapeptides from the Deep South China Sea-Derived Streptomyces scopuliridis SCSIO ZJ46 Active Against Pathogenic Gram-Positive Bacteria.
Journal of Natural Products 77(8):1937 (2014)
Three new cyclohexapeptides, desotamides B-D (2-4), and the known desotamide (1) were isolated from marine microbe Streptomyces scopuliridis SCSIO ZJ46. The sequences and absolute configurations of 2-4 were elucidated on the basis of high-resolution spectroscopic data, Marfey's method, and chira...
Involvement of SgvP in carbon-sulfur bond formation during Griseoviridin biosynthesis.
ChemBioChem 15(8):1183 (2014)
Griseoviridin (GV) is an A-type streptogramin antibiotic displaying antimicrobial activity and acting synergistically with viridogrisein (VG). Bioinformatic analyses reveal SgvP as the sole cytochrome P450 enzyme in the GV/VG gene cluster. To explore the role of SgvP in the GV/VG pathway, we ina...
Cytotoxic and antibacterial marfuraquinocins from the deep South China Sea-derived Streptomyces niveus SCSIO 3406.
Journal of Natural Products 76(12):2263 (2013)
Four new sesquiterpenoid naphthoquinones, marfuraquinocins A-D (1-4), and two new geranylated phenazines, phenaziterpenes A (5) and B (6), were isolated from the fermentation broth of Streptomyces niveus SCSIO 3406, which originated from a South China Sea sediment sample obtained from a depth of...
[Substrate specificity of 3-hydroxypicolinic acid unit in the viridogrisein biosynthetic pathway].
Acta Microbiologica Sinica 53(11):1179 (2013)
To explore the role of sgvS in the biosynthesis of 3-hydroxypicolinic acid moiety of viridogrsein, and to analyze the substrate specificity of 3-hydroxypicolinic acid moiety in the viridogrsein biosynthetic pathway.
Through gene insertion inactivation and in trans complementation strategies, we ...
Discovery of McbB, an enzyme catalyzing the β-carboline skeleton construction in the marinacarboline biosynthetic pathway.
Angewandte Chemie. International edition in Eng... 52(38):9980 (2013)
Three genes, mcbABC, that drive the biosynthesis of marinacarbolines, have been elucidated through genome mining, gene inactivation, heterologous expression, feeding, and site-directed mutagenesis experiments. McbB is highlighted as a novel enzyme for the β-carboline core construction, which inv...
Identification of the grincamycin gene cluster unveils divergent roles for GcnQ in different hosts, tailoring the L-rhodinose moiety.
Organic Letters 15(13):3254 (2013)
The gene cluster responsible for grincamycin (GCN, 1) biosynthesis in Streptomyces lusitanus SCSIO LR32 was identified; heterologous expression of the GCN cluster in S. coelicolor M512 yielded P-1894B (1b) as a predominant product. The ΔgcnQ mutant accumulates intermediate 1a and two shunt produ...
03219A, a new Δ(8,9)-pregnene isolated from Streptomyces sp. SCSIO 03219 obtained from a South China Sea sediment.
Journal of Antibiotics 66(6):327 (2013)
03219A (1), a new pregnene steroid possessing a rare Δ(8,9)-double bond in the skeleton, together with the known naphthoquinone antibiotic (+)-cryptosporin (2) have been isolated from the fermentation broth of Streptomyces sp. SCSIO 03219, which was isolated from a marine sediment collected in t...