Discovery of a pathway for terminal-alkyne amino acid biosynthesis

Marchand, Jorge A.; Neugebauer, Monica E; Ing, M. C.; Lin, Chun‐Hung; Pelton, Jeffrey G.; Chang, Michelle C. Y.

doi:10.1038/s41586-019-1020-y

Cited by 168 publications

(179 citation statements)

References 37 publications

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“…Recently, we reviewed some of the most common reactions that use PLP as a key cofactor in natural products biosynthesis, where the diversity of catalysis is on full display [3]. Since publication of that review, new reactions have been reported, including an exciting new reaction in terminal alkyne biosynthesis catalyzed by BesB [4].…”

Section: Introductionmentioning

confidence: 99%

Emergence of oxygen‐ and pyridoxal phosphate‐dependent reactions

2020

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Pyridoxal 5′‐phosphate (PLP) is an organic cofactor employed by ~ 4% of enzymes. The structure of the PLP cofactor allows for the stabilization of carbanions through resonance. A small number of PLP‐dependent enzymes employ molecular oxygen as a cosubstrate. Here, we review the biological roles and possible mechanisms of these enzymes, and we observe that these enzymes are found in multiple protein families, suggesting that reaction with oxygen might have emerged de novo in several protein families and thus could be directed to emerge again through laboratory evolution experiments.

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Section: Introductionmentioning

confidence: 99%

Emergence of oxygen‐ and pyridoxal phosphate‐dependent reactions

2020

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“…equivalents . Intriguingly, Fe 2+ ‐α‐KG‐dependent halogenases usually accept only substrates that have been tethered to an acyl carrier protein (ACP) or a peptidyl carrier protein (PCP), with WelO5 and BesD being the very rare exceptions known to act directly on stand‐alone substrates.…”

Section: Introductionmentioning

confidence: 99%

An Fe²⁺‐ and α‐Ketoglutarate‐Dependent Halogenase Acts on Nucleotide Substrates

Zhao

Yan

et al. 2020

Angew Chem Int Ed

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While halogenated nucleosides are used as common anticancer and antiviral drugs, naturally occurring halogenated nucleosides are rare. Adechlorin (ade) is a 2′‐chloro nucleoside natural product first identified from Actinomadura sp. ATCC 39365. However, the installation of chlorine in the ade biosynthetic pathway remains elusive. Reported herein is a Fe2+‐α‐ketoglutarate halogenase AdeV that can install a chlorine atom at the C2′ position of 2′‐deoxyadenosine monophosphate to afford 2′‐chloro‐2′‐deoxyadenosine monophosphate. Furthermore, 2′,3′‐dideoxyadenosine‐5′‐monophosphate and 2′‐deoxyinosine‐5′‐monophosphate can also be converted, albeit 20‐fold and 2‐fold, respectively, less efficiently relative to the conversion of 2′‐deoxyadenosine monophosphate. AdeV represents the first example of a Fe2+‐α‐ketoglutarate‐dependent halogenase that converts nucleotides into chlorinated analogues.

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“…42 In addition, researchers use dehydration of the near-terminal hydroxyl group, 43,44 and a recently discovered new biochemical reaction class forms a terminal double bond, releasing ammonia and formaldehyde. 45,46 FDC, which contains a new cofactor prFMN with co-expression of prenyltransferase, is a key enzyme for 1,3-butadiene production, and prFMNcontaining FDC can catalyze decarboxylation of a carboxylic group bonding to the C-C double bond.…”

Section: Discussionmentioning

confidence: 99%

Direct 1,3-butadiene biosynthesis in Escherichia coli via a tailored ferulic acid decarboxylase mutant

Mori

Noda

Shirai

et al. 2020

Preprint

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The C4 unsaturated compound 1,3-butadiene is an important monomer in synthetic rubber and engineering plastic production. However, microorganisms cannot directly produce 1,3-butadiene using glucose as a renewable carbon source via biological processes. This study constructed a novel artificial metabolic pathway for 1,3-butadiene production from glucose in Escherichia coli by combining the cis,cis-muconic acid (ccMA)-producing pathway and tailored ferulic acid decarboxylase mutants. The rational enzyme design of the substrate-binding site by computational simulation improved 1,3-butadiene-producing ccMA decarboxylation with a small mutant library. We found that changing dissolved oxygen and controlling pH were important factors for 1,3-butadiene production. Using dissolved oxygen–stat fed-batch fermentation in a 1-L jar fermenter, we could produce 2.1 g L− 1 of 1,3-butadiene. These results indicated that using a rational enzyme design, we can produce unnatural/nonbiological compounds (those that are made from petroleum and cannot be produced by microorganisms) using glucose as a renewable carbon source.

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Discovery of a pathway for terminal-alkyne amino acid biosynthesis

Cited by 168 publications

References 37 publications

Emergence of oxygen‐ and pyridoxal phosphate‐dependent reactions

Emergence of oxygen‐ and pyridoxal phosphate‐dependent reactions

An Fe²⁺‐ and α‐Ketoglutarate‐Dependent Halogenase Acts on Nucleotide Substrates

Direct 1,3-butadiene biosynthesis in Escherichia coli via a tailored ferulic acid decarboxylase mutant

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Discovery of a pathway for terminal-alkyne amino acid biosynthesis

Cited by 168 publications

References 37 publications

Emergence of oxygen‐ and pyridoxal phosphate‐dependent reactions

Emergence of oxygen‐ and pyridoxal phosphate‐dependent reactions

An Fe2+‐ and α‐Ketoglutarate‐Dependent Halogenase Acts on Nucleotide Substrates

Direct 1,3-butadiene biosynthesis in Escherichia coli via a tailored ferulic acid decarboxylase mutant

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An Fe²⁺‐ and α‐Ketoglutarate‐Dependent Halogenase Acts on Nucleotide Substrates