Enzymatic routes to enantiomerically enriched 1-butene oxide

Chenault, H. Keith; Kim, Mahn Joo; Akiyama, Alan; Miyazawa, Toshifumi; Simon, Ethan S.; Whitesides, George M.

doi:10.1021/jo00388a054

Cited by 35 publications

(21 citation statements)

References 1 publication

(1 reference statement)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…0.92 g( 99.6 % ee,9 0% yield for the reaction with sodium formate) and 0.95 g( 99.6 % ee,9 2% yield for the reaction with ammonium formate) d-2-amino butyric acid were obtained, respectively. 1…”

Section: Optimization Of Tri-enzymatic Reaction Systemmentioning

confidence: 99%

“…Generally speaking, resolution of the racemate of α‐amino acids is currently the main method to obtain the optically pure d ‐amino acids. For d ‐2‐aminobutyric acid, aminoacylase, protease, or the formation of diastereomeric derivatives have been used to realize the separation of l / d ‐amino acids. ω‐Transaminases have been used for the synthesis of d ‐2‐aminobutyric acid through the amino‐transfer reaction, providing an alternative biocatalytic method .…”

Section: Introductionmentioning

confidence: 99%

“…Although d ‐α‐amino acids do not exist in the nature as widely as their l ‐counterparts, naturally occurring d ‐α‐amino acids play an important role in defence mechanisms (cell wall, venoms) of many microorganisms and plants . d ‐α‐Amino acids have also been detected in a variety of peptides synthesized by animal cells and in human tissue, appearing as indicators of aging .…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Highly Atom Economic Synthesis of d‐2‐Aminobutyric Acid through an In Vitro Tri‐enzymatic Catalytic System

et al. 2017

View full text Add to dashboard Cite

d‐2‐Aminobutyric acid is an unnatural amino acid serving as an important intermediate in pharmaceutical production. Developing a synthetic method that uses cheaper starting materials and produces less by‐product is a pressing demand. A tri‐enzymatic catalytic system, which is composed of l‐threonine ammonia lyase (l‐TAL), d‐amino acid dehydrogenase (d‐AADH), and formate dehydrogenase (FDH), has thus been developed for the synthesis of d‐2‐aminobutyric acid with high optical purity. In this cascade reaction, the readily available l‐threonine serves as the starting material, carbon dioxide and water are the by‐products. d‐2‐Aminobutyric acid was obtained with >90 % yield and >99 % enantioselective excess, even without adding external ammonia, demonstrating that the ammonia from the first reaction can serve as the amino donor for the reductive amination step. This multi‐enzymatic system provides an attractive method with high atomic economy for the synthesis of d‐α‐amino acids from the corresponding l‐α‐amino acids, which are readily produced by fermentation.

show abstract

Section: Optimization Of Tri-enzymatic Reaction Systemmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Highly Atom Economic Synthesis of d‐2‐Aminobutyric Acid through an In Vitro Tri‐enzymatic Catalytic System

et al. 2017

View full text Add to dashboard Cite

show abstract

“…Because the specific (−)‐rotation of ( S )‐ 3 and (+)‐rotation of ( R )‐ 3a is known , and perfect retention of the configuration is supposed, the corresponding absolute configurations of the major/minor enantiomers of all products ( 2 , 2a , and 3a ) can also be given. On the basis of the integrals of the chiral‐GC measurements, it can be stated that the first eluted enantiomers of 1 , 2 , and 3 are equally possessing S absolute configuration.…”

Section: Resultsmentioning

confidence: 99%

“…(R)‐(+)‐1,2‐Dihydroxybutane ( 3a ) : colorless liquid; δ H (500 MHz, D 2 O) 3.49 (2 H, C H a H b OH and C H OH), 3.35 (1 H, dd, 6.6 Hz, 11.3 Hz C H a H b OH), 1.41 (1 H, m, C H 2 CH 3 ), 0.80 (3 H, t, 7.5 Hz, CH 3 ); δ C (125.7 MHz, D 2 O) 73.7, 66.3, 26.0, 10.0; IR (KBr (cm −1 )) 3375. MS m/z (rel int.…”

Section: Methodsmentioning

confidence: 99%

Asymmetric Hydroformylation of 4‐Vinyl‐1,3‐dioxolan‐2‐one

Pongrácz

Kollár

2016

Journal of Heterocyclic Chem

View full text Add to dashboard Cite

A chiral cyclic carbonate, 4‐vinyl‐1,3‐dioxolan‐2‐one was used as racemic substrate in asymmetric hydroformylation. The catalysts were formed in situ from “pre‐formed” PtCl2(diphosphine) and tin(II) chloride. (2S,4S)‐2,4‐Bis(diphenylphosphinopentane ((S,S)‐BDPP)), (S,S)‐2,3‐O‐izopropylidine‐2,3‐dihydroxy‐1,4‐bis(diphenylphosphino)butane ((S,S)‐DIOP)), and (R)‐2,2′‐bis(diphenylphosphino)‐1,1′‐binaphthyl ((R)‐BINAP)) were used as optically active diphosphine ligands. The platinum‐containing catalytic systems provided surprisingly high activity. The hydroformylation selectivities of up to 97% were accompanied by perfect regioselectivity towards the dioxolane‐based linear aldehyde. The enantiomeric composition of all components in the reaction mixture was determined and followed throughout the reaction. The unreacted 4‐vinyl‐1,3‐dioxolan‐2‐one was recovered in optically active form. The kinetic resolution was rationalized using the enantiomeric composition of the substrate and the products.

show abstract