The studies on chemoselective promiscuous activity of hydrolases on acylals transformations

Koszelewski, Dominik; Ostaszewski, Ryszard

doi:10.1016/j.bioorg.2019.02.050

Cited by 8 publications

(14 citation statements)

References 151 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Bovine serum albumin was purchased from Sigma-Aldrich. Pig liver esterase acetone powder was obtained according to the published procedure . 4-Nitrobenzylidene diacetate (catalog no.…”

Section: Methodssupporting

confidence: 89%

“…The impact of the type of acylal 2 on the acylation reaction was further investigated (Figure ). Eight various donors 2b – i were prepared according to the literature procedure and used with the model benzyl alcohol ( 1a ) in MTBE at 40 °C. The obtained results are summarized in Table .…”

Section: Resultsmentioning

confidence: 99%

“…However, a long reaction time was required to obtain certain acetates in satisfying yields . Recently, we have shown that gem -acetates (1,1-diacetates), which are carbonyl surrogates, can be effectively deprotected by hydrolases under aqueous conditions to the parent aldehydes . As part of our ongoing research on environmentally sustainable protocols, we devoted our attention to develop protocols toward acetates, which combines both economic and green chemistry aspects.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio- and Stereoselective Acylation of Alcohols

et al. 2021

Self Cite

View full text Add to dashboard Cite

Geminal diacetates have been used as sustainable acyl donors for enzymatic acylation of chiral and nonchiral alcohols. Especially, it was revealed that geminal diacetates showed higher reactivity than vinyl acetate for hydrolases that are sensitive to acetaldehyde. Under optimized conditions for enzymatic acylation, several synthetically relevant saturated and unsaturated acetates of various primary alcohols were obtained in very high yields up to 98% without E/Z isomerization of the double bond. Subsequently, the acyl donor was recreated from the resulting aldehyde and reused constantly in acylation. Therefore, the developed process is characterized by high atomic efficiency. Moreover, it was shown that acylation using geminal diacetates resulted in remarkable regioselectivity by discriminating among the primary and secondary hydroxyl groups in 1-phenyl-1,3-propanediol providing exclusively 3-acetoxy-1-phenyl-propan-1-ol in good yield. Further, enzymatic kinetic resolution (EKR) and chemoenzymatic dynamic kinetic resolution (DKR) protocols were developed using geminal diacetate as an acylating agent, resulting in chiral acetates in high yields up to 94% with enantiomeric excesses exceeding 99%.

show abstract

“…Bovine serum albumin was purchased from Sigma-Aldrich. Pig liver esterase acetone powder was obtained according to the published procedure . 4-Nitrobenzylidene diacetate (catalog no.…”

Section: Methodssupporting

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio- and Stereoselective Acylation of Alcohols

et al. 2021

Self Cite

View full text Add to dashboard Cite

show abstract

“…The Kabachnik–Fields reaction is the most efficient method for the formation of carbon−phosphorus bonds using an aldehyde, amine, and H -phosphite. A number of other synthetic approaches have also been reported for the preparation of α-aminophosphonates [ 7 , 50 , 51 , 52 , 53 , 54 , 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 , 64 , 65 , 66 , 67 , 68 , 69 , 70 , 71 , 72 , 73 , 74 , 75 , 76 , 77 , 78 , 79 , 80 , 81 , 82 , 83 , 84 , 85 , 86 , 87 , 88 , 89 , 90 , 91 , 92 , 93 , 94 , 95 ]. These methods are generally conducted in the presence of various organic and inorganic bases [ 56 , 57 , ...…”

Section: Resultsmentioning

confidence: 99%

“…As a continuation of our research on seeking new catalytic activities of hydrolases [ 74 , 75 , 76 , 77 , 78 , 79 , 80 , 94 , 95 ], we focused our efforts on elaborating a sustainable metal-free method towards desired α-aminophosphonates 1 – 16 ( Figure 2 ).…”

Section: Resultsmentioning

confidence: 99%

Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reaction

et al. 2022

Self Cite

View full text Add to dashboard Cite

We reported a new method dealing with the synthesis of novel pharmacologically relevant α-aminophosphonate derivatives via a lipase-catalyzed Kabachnik−Fields reaction with yields of up to 93%. The advantages of this protocol are excellent yields, mild reaction conditions, low costs, and sustainability. The developed protocol is applicable to a range of H-phosphites and organic amines, providing a wide substrate scope. A new class of α-aminophosphonate analogues possessing P-chiral centers was also synthesized. The synthesized compounds were characterized on the basis of their antimicrobial activities against E. coli. The impact of the various alkoxy groups on antimicrobial activity was demonstrated. The crucial role of the substituents, located at the aromatic rings in the phenylethyloxy and benzyloxy groups, on the inhibitory action against selected pathogenic E. coli strains was revealed. The observed results are especially important because of increasing resistance of bacteria to various drugs and antibiotics.

show abstract

Diversified upgrading of HMF via acetylation, aldol condensation, carboxymethylation, vinylation and reductive amination reactions

Rigo

Polidoro

Perosa

et al. 2021

Molecular Catalysis

View full text Add to dashboard Cite

The studies on chemoselective promiscuous activity of hydrolases on acylals transformations

Cited by 8 publications

References 151 publications

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio- and Stereoselective Acylation of Alcohols

Evaluation of gem-Diacetates as Alternative Reagents for Enzymatic Regio- and Stereoselective Acylation of Alcohols

Relationship between Structure and Antibacterial Activity of α-Aminophosphonate Derivatives Obtained via Lipase-Catalyzed Kabachnik−Fields Reaction

Diversified upgrading of HMF via acetylation, aldol condensation, carboxymethylation, vinylation and reductive amination reactions

Contact Info

Product

Resources

About