Class II terpene cyclases: structures, mechanisms, and engineering

Pan, Xingming; Rudolf, Jeffrey D.; Dong, Liao-Bin

doi:10.1039/d3np00033h

Cited by 7 publications

(3 citation statements)

References 176 publications

(498 reference statements)

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“…This marks the first discovery of natural DMTs from bacteria, surpassing previous findings of bacterial DMSs which focused only on the enzyme itself without reporting natural DMT or exploring associated BGCs [ 17 ]. Additionally, while drimentines, bacterial meroterpenoids, share the drimanyl scaffold, their biosynthetic pathways, particularly the terpene cyclases synthesizing the drimanyl structures, show substantial divergence from DMT pathways [ 21 , 30 – 32 ]. This fundamental difference in biosynthetic mechanisms serves to categorize DMSs and drimentines into distinct subfamilies within the sesquiterpenoids.…”

Section: Resultsmentioning

confidence: 99%

“…In the biosynthesis of calidoustene C, DrtB from Aspergillus calidoustus functions as a dual-functional enzyme, comprising two domains: a HAD-like hydrolase domain fused with a terpene cyclase domain. Initially, FPP is cyclized into the drimenyl diphosphate in a class II terpene cyclase manner, which is then processed by the hydrolase domain to form drimenol [ 21 ]. Subsequently, this molecule undergoes further modifications by two cytochrome P450s monooxygenases (P450s, DrtC and DrtD) and one acyltransferase (DrtE) to produce calidoustene C [ 13 ].…”

Section: Introductionmentioning

confidence: 99%

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Discovery and biosynthesis of bacterial drimane-type sesquiterpenoids from Streptomyces clavuligerus

Zhang,

Du,

Pan

et al. 2024

Beilstein J. Org. Chem.

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Drimane-type sesquiterpenoids (DMTs) are characterized by a distinctive 6/6 bicyclic skeleton comprising the A and B rings. While DMTs are commonly found in fungi and plants, their presence in bacteria has not been reported. Moreover, the biosynthetic pathways for DMTs have been primarily elucidated in fungi, with identified P450s only acting on the B ring. In this study, we isolated and characterized three bacterial DMTs, namely 3β-hydroxydrimenol (2), 2α-hydroxydrimenol (3), and 3-ketodrimenol (4), from Streptomyces clavuligerus. Through genome mining and heterologous expression, we identified a cav biosynthetic gene cluster responsible for the biosynthesis of DMTs 2–4, along with a P450, CavA, responsible for introducing the C-2 and C-3 hydroxy groups. Furthermore, the substrate scope of CavA revealed its ability to hydroxylate drimenol analogs. This discovery not only broadens the known chemical diversity of DMTs from bacteria, but also provides new insights into DMT biosynthesis in bacteria.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Discovery and biosynthesis of bacterial drimane-type sesquiterpenoids from Streptomyces clavuligerus

Zhang,

Du,

Pan

et al. 2024

Beilstein J. Org. Chem.

Self Cite

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show abstract

“…[24][25][26][27][28][29] In fact, skeletal reorganization is one of the most important tools used by nature to generate the huge variety of natural products. [30][31][32][33] Skeletal reorganization can utilize either a natural product or a human-made synthetic intermediate as a substrate. In the former case, generation of target molecules by skeletal reorganization of inexpensive commercially available compounds derived from natural sources is oen inspired by proposed biosynthetic pathways.…”

Section: Introductionmentioning

confidence: 99%