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Genome Mining of Terpene Synthases from Fourteen Streptomyces Strains Open
Terpenoids are the most structurally diverse class of natural products (NPs). Despite their abundance, the functional diversity of bacterial terpene synthases (TPSs), particularly from Streptomyces species, remains largely unexplored. In t…
View article: Production of Aniline Derivatives from <i>Cladosporium cladosporioides</i> TFU‐13 and <i>Volutella</i> sp. TFU‐28 in the Presence of SAHA
Production of Aniline Derivatives from <i>Cladosporium cladosporioides</i> TFU‐13 and <i>Volutella</i> sp. TFU‐28 in the Presence of SAHA Open
Biotransformation of suberoylanilide hydroxamic acid (SAHA) by soil‐derived Cladosporium cladosporioides TFU‐13 and Volutella sp. TFU‐28 yielded a panel of aniline derivatives, including two new metabolites ( 1 and 4 ) and six previously r…
Cladosporin, A Highly Potent Antimalaria Drug? Open
Cladosporin, a unique natural product from the fungus Cladosporium cladosporioides , exhibits nanomolar inhibitory activity against Plasmodium falciparum by targeting its cytosolic lysyl‐tRNA synthetase ( Pf KRS) to inhibit protein biosynt…
View article: The stereochemical course of 2-methylisoborneol biosynthesis
The stereochemical course of 2-methylisoborneol biosynthesis Open
Both enantiomers of 2-methyllinalyl diphosphate (2-Me-LPP) were synthesized enantioselectively using Sharpless epoxidation as a key step and purification of enantiomerically enriched intermediates through HPLC separation on a chiral statio…
Deceptive Complexity in Formation of Cleistantha-8,12-diene Open
A barley diterpene synthase (HvKSL4) was found to produce (14S)-cleistantha-8,12-diene (1). Formation of the nearly planar cyclohexa-1,4-diene configuration leaves the ring poised for aromatization, but necessitates a deceptively complicat…
Mechanism of the Bifunctional Multiple Product Sesterterpene Synthase AcAS from <i>Aspergillus calidoustus</i> Open
The multiproduct chimeric sesterterpene synthase AcAS from Aspergillus calidoustus yielded spirocyclic calidoustene, which exhibits a novel skeleton, besides five known sesterterpenes. The complex cyclisation mechanism to all six compounds…
The EI‐MS Fragmentation Mechanisms of the Bacterial Diterpenes Polytrichastrene A and Wanju‐2,5‐diene Open
The fragmentation mechanisms leading to the formation of several pronounced fragment ions formed during EI mass spectrometry of the diterpene hydrocarbons polytrichastrene A and wanju‐2,5‐diene were investigated by isotopic labelling exper…
Targeting active site residues and structural anchoring positions in terpene synthases Open
The sesterterpene synthase SmTS1 from Streptomyces mobaraensis contains several unusual residues in positions that are otherwise highly conserved. Site-directed mutagenesis experiments for these residues are reported that showed different …
Using Terpene Synthase Plasticity in Catalysis: On the Enzymatic Conversion of Synthetic Farnesyl Diphosphate Analogues Open
Four synthetic farnesyl diphosphate analogues were enzymatically converted with three bacterial sesquiterpene synthases, including β‐himachalene synthase (HcS) and ( Z )‐γ‐bisabolene synthase (BbS) from Cryptosporangium arvum , and germacr…
Functional Switch and Ethyl Group Formation in the Bacterial Polytrichastrene Synthase from <i>Chryseobacterium polytrichastri</i> Open
A reinvestigation of the linalool synthase from Chryseobacterium polytrichastri uncovered its diterpene synthase activity, yielding polytrichastrene A and polytrichastrol A with new skeletons, besides known wanju‐2,5‐diene and thunbergol. …
A Flavoprotein Dioxygenase Steers Bacterial Tropone Biosynthesis via Coenzyme A-Ester Oxygenolysis and Ring Epoxidation Open
Bacterial tropone natural products such as tropolone, tropodithietic acid, or the roseobacticides play crucial roles in various terrestrial and marine symbiotic interactions as virulence factors, antibiotics, algaecides, or quorum sensing …
Rerouting and Improving Dauc‐8‐en‐11‐ol Synthase from <i>Streptomyces venezuelae</i> to a High Yielding Biocatalyst Open
The dauc‐8‐en‐11‐ol synthase from Streptomyces venezuelae was investigated for its catalytic activity towards alternative terpene precursors, specifically designed to enable new cyclisation pathways. Exchange of aromatic amino acid residue…
On the mass spectrometric fragmentations of the bacterial sesterterpenes sestermobaraenes A–C Open
A 13 C-labelling was introduced into each individual carbon of the recently discovered sestermobaraenes by the enzymatic conversion of the correspondingly 13 C-labelled isoprenyl diphosphate precursors with the sestermobaraene synthase fro…
Discovery of the cryptic function of terpene cyclases as aromatic prenyltransferases Open
Catalytic versatility is an inherent property of many enzymes. In nature, terpene cyclases comprise the foundation of molecular biodiversity as they generate diverse hydrocarbon scaffolds found in thousands of terpenoid natural products. H…
The Biosynthetic Gene Cluster for Sestermobaraenes—Discovery of a Geranylfarnesyl Diphosphate Synthase and a Multiproduct Sesterterpene Synthase from <i>Streptomyces mobaraensis</i> Open
A biosynthetic gene cluster from Streptomyces mobaraensis encoding the first cases of a bacterial geranylfarnesyl diphosphate synthase and a type I sesterterpene synthase was identified. The structures of seven sesterterpenes produced by t…
Enzymatic Synthesis of Methylated Terpene Analogues Using the Plasticity of Bacterial Terpene Synthases Open
Methylated analogues of isopentenyl diphosphate were synthesised and enzymatically incorporated into methylated terpenes. A detailed stereochemical analysis of the obtained products is presented. The methylated terpene precursors were also…
Releasing the potential power of terpene synthases by a robust precursor supply platform Open
Terpenoids represent the largest family of natural products. Their structural diversity is largely due to variable skeletons generated by terpene synthases. However, terpene skeletons found in nature are much more than those generated from…
Releasing potential power of terpene synthases by a robust precursor supply platform Open
Approximately 76,000 discovered makes terpenoids the largest family of natural products in nature with widespread applications. The wide-spectrum of structural diversity of the terpenoids were largely due to the variable skeletons generate…