Exploiting the Potential of Meroterpenoid Cyclases to Expand the Chemical Space of Fungal Meroterpenoids

Mitsuhashi, Tsutomu; Barra, Lena; Powers, Zachary; Kojasoy, Volga; Cheng, Andrea; Yang, Feng; Taniguchi, Yoshimasa; Kikuchi, Takashi; Fujita, Makoto; Tantillo, Dean J.; Porco, John A.; Abe, Ikuro

doi:10.1002/anie.202011171

Cited by 32 publications

(26 citation statements)

References 66 publications

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“…Later on, the Dickschat group [154] demonstrated that bacterial terpene synthases could cyclize methylated IPP analogues. Recently, Porco, Abe and coworkers [155] evaluated the substrate promiscuity of fungal meroterpenoid cyclases in the early structural diversity‐generating steps of fungal meroterpenoid biosynthetic pathways (Scheme 36b). Using this approach, 12 unnatural meroterpenoids were accessed chemoenzymatically from synthetic substrates.…”

Section: Complementary Methods/future Directionsmentioning

confidence: 99%

Practical Enzymatic Production of Carbocycles

Wang

Taber

Renata

2021

Chemistry A European J

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The Pd‐catalyzed carbon‐carbon bond formation pioneered by Heck in 1969 has dominated medicinal chemistry development for the ensuing fifty years. As the demand for more complex three‐dimensional active pharmaceuticals continues to increase, preparative enzyme‐mediated assembly, by virtue of its exquisite selectivity and sustainable nature, is poised to provide a practical and affordable alternative for accessing such compounds. In this minireview, we summarize recent state‐of‐the‐art developments in practical enzyme‐mediated assembly of carbocycles. When appropriate, background information on the enzymatic transformation is provided and challenges and/or limitations are also highlighted.

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Section: Complementary Methods/future Directionsmentioning

confidence: 99%

Practical Enzymatic Production of Carbocycles

Wang

Taber

Renata

2021

Chemistry A European J

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“…AndB, the dedicated non-canonical terpene cyclase from the and BGC, was shown to convert the unnatural DMOA-derived substrates 68 and 70 into the novel meroterpenoids 69 and 71, respectively, with 71 displaying an unprecedented 6,5,5,6-tetracyclic ring system. 87 The derived novel cyclase products will enable further downstream tailoring.…”

Section: Anditomin and Related Meroterpenoidsmentioning

confidence: 99%

“…In fact, the mutasynthetic studies with AndB were part of a larger study that investigated the potential of nine non-canonical meroterpenoid cyclases to convert unnatural substrate analogues, resulting in the formation of twelve novel meroterpenoids and emphasizing the power of this strategy to drive structural diversification of fungal meroterpenoids. 87…”

Section: Anditomin and Related Meroterpenoidsmentioning

confidence: 99%

Total Mycosynthesis: Rational Bioconstruction and Bioengineering of Fungal Natural Products

2021

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“… 52 Abe, Porco, Tantillo, Fujita, et al used the same MOF to determine the structures of meroterpenoids chemoenzymatically synthesized using fungal meroterpenoid cyclases. 53 For mechanistic studies, Fujita et al used a variant of 1 to examine Pd-catalyzed aryl brominations via SC-XRD. 54 ZnI 2 , tpt, and a palladacycle (dibenzo[ f , h ]quinolinyl Pd(II) methylxanthate) were cocrystallized, and subsequent solvent exchange with MeCN provided a crystalline flask for time-course studies that involved soaking with N -bromosuccinimide.…”

Section: Diversity Of Crystalline Matricesmentioning

confidence: 99%

Application of Crystalline Matrices for the Structural Determination of Organic Molecules

Cardenal

Ramadhar

2021

ACS Cent. Sci.

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While single-crystal X-ray diffraction (SC-XRD) is one of the most powerful structural determination techniques for organic molecules, the requirement of obtaining a suitable crystal for analysis limits its applicability, particularly for liquids and amorphous solids. The emergent use of preformed porous crystalline matrices that can absorb organic compounds and stabilize them via host–guest interactions for observation via SC-XRD offers a way to overcome this hindrance. A topical and current discussion of SC-XRD in organic chemistry and the use of preformed matrices for the in crystallo analysis of organic compounds, with a particular focus on the absolute structure determination of chiral molecules, is presented. Preformed crystalline matrices that are covered include metal–organic frameworks (MOFs) as used in the crystalline sponge method, metal–organic polyhedra (MOPs, coordination cages), porous organic materials (POMs)/porous organic molecular crystals (POMCs), and biological scaffolds. An outlook and perspective on the current technology and on its future directions is provided.

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Exploiting the Potential of Meroterpenoid Cyclases to Expand the Chemical Space of Fungal Meroterpenoids

Abstract: OpenBU http://open.bu.edu Chemistry BU Open Access Articles 2020-09-15 Exploiting the potential of meroterpenoid cyclases to expand the chemical space of fun...

Cited by 32 publications

References 66 publications

Practical Enzymatic Production of Carbocycles

Practical Enzymatic Production of Carbocycles

Total Mycosynthesis: Rational Bioconstruction and Bioengineering of Fungal Natural Products

Application of Crystalline Matrices for the Structural Determination of Organic Molecules

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