Production of chiral β-amino acids using ω-transaminase from Burkholderia graminis

Mathew, Sam; Bea, Han-Seop; Nadarajan, Sivakumar; Chung, Taeowan; Yun, Hyungdon

doi:10.1016/j.jbiotec.2015.01.011

Cited by 34 publications

(33 citation statements)

References 21 publications

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“…To detect the acetophenone from ω‐TA reactions, enzyme reactions were stopped by adding 10% perchloric acid (50% v/v). After centrifuging (14,000 rpm, 15 min), the samples were analyzed by high‐performance liquid chromatography (HPLC [YL9100, Young Lin, Korea]) as described previously …”

Section: Methodsmentioning

confidence: 99%

Biosynthesis of the Nylon 12 Monomer, ω‐Aminododecanoic Acid with Novel CYP153A, AlkJ, and ω‐TA Enzymes

Ahsan

Jeon

Nadarajan

et al. 2018

Biotechnology Journal

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Bioplastics are derived from renewable biomass sources, such as vegetable oils, cellulose, and starches. An important and high-performance member of the bioplastic family is Nylon 12. The biosynthesis of ω-amino dodecanoic acid (ω-AmDDA), the monomer of Nylon 12 from vegetable oil derivatives is considered as an alternative to petroleum-based monomer synthesis. In this study, for the production of ω-AmDDA from dodecanoic acid (DDA), the cascade of novel P450 (CYP153A), alcohol dehydrogenase (AlkJ), and ω-transaminase (ω-TA) is developed. The regioselective ω-hydroxylation of 1 mM DDA with near complete conversion (>99%) is achieved using a whole-cell biocatalyst co-expressing CYP153A, ferredoxin reductase and ferredoxin. When the consecutive biotransformation of ω-hydroxy dodecanoic acid (ω-OHDDA) is carried out using a whole-cell biocatalyst co-expressing AlkJ and ω-TA, 1.8 mM ω-OHDDA is converted into ω-AmDDA with 87% conversion in 3 h. Finally, when a one-pot reaction is carried out with 2 mM DDA using both whole-cell systems, 0.6 mM ω-AmDDA is produced after a 5 h reaction. The results demonstrated the scope of the potential cascade reaction of novel CYP153A, AlkJ, and ω-TA for the production of industrially important bioplastic monomers, amino fatty acids, from FFAs.

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Section: Methodsmentioning

confidence: 99%

Biosynthesis of the Nylon 12 Monomer, ω‐Aminododecanoic Acid with Novel CYP153A, AlkJ, and ω‐TA Enzymes

Ahsan

Jeon

Nadarajan

et al. 2018

Biotechnology Journal

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“…Zuschriften resolutions, [7] as well as by using chiral auxiliaries in such methods as enolate addition to imidoyl chlorides [6a] and chiral lithium amide conjugated addition.…”

Section: Angewandte Chemiementioning

confidence: 99%

“…[1b,2] As examples,c ispentacin and icofungipen exhibit noteworthy antifungal and antibacterial activities, [3] trans-aminocyclopentanecarboxylic acid [(1R,2R)-ACPC] has been applied for constructing b-peptide antibiotics, [4] and amipurimycin is active against Pyricularia oryzae. [2] However,m ost methodologies have focused on stoichiometric asymmetric synthesis [6] or resolution, [7] and few have provided highly enantioselective access to highly functionalized substrates. [2] However,m ost methodologies have focused on stoichiometric asymmetric synthesis [6] or resolution, [7] and few have provided highly enantioselective access to highly functionalized substrates.…”

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confidence: 99%

Catalytic Asymmetric Synthesis of Cyclopentyl β‐Amino Esters by [3+2] Cycloaddition of Enecarbamates with Electrophilic Metalloenolcarbene Intermediates

et al. 2016

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Chiral cyclopentyl β-amino esters are formed catalytically by [3+2] cycloaddition reactions of enecarbamates with electrophilic metalloenolcarbenes in high yield with up to 98 % ee and excellent diastereocontrol. Use of β-silyl-substituted enoldiazoacetates with a chiral dirhodium catalyst and trans-β-arylvinylcarbamates are optimal for this transformation, which occurs with hydrogen-bond association between the vinylcarbamate and the intermediate metalloenolcarbene. Reductive conversion of the protected amino esters forms highly functionalized cyclopentyl β-amino acids and 3-aminocyclopentanones.

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“…[5] As ac onsequence of their high biological potential, significant effort has been devoted to asymmetric syntheses of cyclo-pentyl b-amino acids and their derivatives. [2] However,m ost methodologies have focused on stoichiometric asymmetric synthesis [6] or resolution, [7] and few have provided highly enantioselective access to highly functionalized substrates. [8] Recently,metalloenolcarbenes which are generated catalytically from stable enoldiazo compounds have emerged as asynthetically useful class of carbene precursors when paired with transition-metal catalysts.…”

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confidence: 99%

“…N either copper [Cu(MeCN) 4 BF 4 ]n or silver (AgSbF 6 )c atalysts were effective for this reaction, and enoldiazoacetamides were unreactive towards enecarbamates under these catalytic conditions. Tr aditionally,t he asymmetric synthesis of cyclopentyl bamino acids have been achieved by using enzymatic or kinetic resolutions, [7] as well as by using chiral auxiliaries in such methods as enolate addition to imidoyl chlorides [6a] and chiral lithium amide conjugated addition. [6b] Thec atalytic asymmetric hydrogenation of cyclic b-(acylamino) acrylates provides an efficient approach to chiral carbocyclic b-amino esters,b ut only applications to unsubstituted cyclopentyl bamino esters have been reported.…”

mentioning

confidence: 99%

Catalytic Asymmetric Synthesis of Cyclopentyl β‐Amino Esters by [3+2] Cycloaddition of Enecarbamates with Electrophilic Metalloenolcarbene Intermediates

et al. 2016

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Chiral cyclopentyl b-amino esters are formed catalytically by [3+ +2] cycloaddition reactions of enecarbamates with electrophilic metalloenolcarbenes in high yield with up to 98 %e ea nd excellent diastereocontrol. Use of b-silylsubstituted enoldiazoacetates with ac hiral dirhodium catalyst and trans-b-arylvinylcarbamates are optimal for this transformation, which occurs with hydrogen-bond association between the vinylcarbamate and the intermediate metalloenolcarbene.R eductive conversion of the protected amino esters forms highly functionalizedc yclopentyl b-amino acids and 3aminocyclopentanones. Scheme 1. Bioactive cyclopentyl b-amino acids and derivatives. Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under http://dx.doi.org/10. 1002/anie.201605438. Angewandte Chemie Communications Scheme 5. Reaction results of cis-2a and 7.D isfavoredtransition state of [3+ +2] cycloaddition of cis-b-phenylvinylcarbamate. Angewandte Chemie Communications

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Production of chiral β-amino acids using ω-transaminase from Burkholderia graminis

Cited by 34 publications

References 21 publications

Biosynthesis of the Nylon 12 Monomer, ω‐Aminododecanoic Acid with Novel CYP153A, AlkJ, and ω‐TA Enzymes

Biosynthesis of the Nylon 12 Monomer, ω‐Aminododecanoic Acid with Novel CYP153A, AlkJ, and ω‐TA Enzymes

Catalytic Asymmetric Synthesis of Cyclopentyl β‐Amino Esters by [3+2] Cycloaddition of Enecarbamates with Electrophilic Metalloenolcarbene Intermediates

Catalytic Asymmetric Synthesis of Cyclopentyl β‐Amino Esters by [3+2] Cycloaddition of Enecarbamates with Electrophilic Metalloenolcarbene Intermediates

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