Synthesis of Chiral 5‐Aryl‐2‐oxazolidinones via Halohydrin Dehalogenase‐Catalyzed Enantio‐ and Regioselective Ring‐Opening of Styrene Oxides

2020 ◽  
Vol 362 (5) ◽  
pp. 1201-1207 ◽  
Author(s):  
Nanwei Wan ◽  
Xiaoying Zhou ◽  
Ran Ma ◽  
Jiawei Tian ◽  
Huihui Wang ◽  
...  
Keyword(s):  
Ring Opening ◽  
Halohydrin Dehalogenase

scholarly journals Highly α-position regioselective ring-opening of epoxides catalyzed by halohydrin dehalogenase from Ilumatobacter coccineus: a biocatalytic approach to 2-azido-2-aryl-1-ols

RSC Advances ◽  
2019 ◽  
Vol 9 (29) ◽  
pp. 16418-16422 ◽  
Author(s):  
Miao An ◽  
Wanyi Liu ◽  
Xiaoying Zhou ◽  
Ran Ma ◽  
Huihui Wang ◽  
...  
Keyword(s):  
Ring Opening ◽  
Styrene Oxide ◽  
Halohydrin Dehalogenase ◽  
Ring Opening Of Epoxides

Biocatalytic synthesis of 2-azido-2-aryl-1-ols was achieved via HheG-catalyzed α-position regioselective ring-opening of styrene oxide derivatives.

Regioselective Ring‐Opening of Styrene Oxide Derivatives Using Halohydrin Dehalogenase for Synthesis of 4‐Aryloxazolidinones

2019 ◽  
Vol 361 (20) ◽  
pp. 4651-4655 ◽  
Author(s):  
Nanwei Wan ◽  
Jiawei Tian ◽  
Xiaoying Zhou ◽  
Huihui Wang ◽  
Baodong Cui ◽  
...  
Keyword(s):  
Ring Opening ◽  
Styrene Oxide ◽  
Halohydrin Dehalogenase

Catalytic Promiscuity of Halohydrin Dehalogenase and its Application in Enantioselective Epoxide Ring Opening

ChemBioChem ◽  
2008 ◽  
Vol 9 (7) ◽  
pp. 1048-1051 ◽  
Author(s):  
Ghannia Hasnaoui-Dijoux ◽  
Maja Majerić Elenkov ◽  
Jeffrey H. Lutje Spelberg ◽  
Bernhard Hauer ◽  
Dick B. Janssen
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Catalytic Promiscuity ◽  
Epoxide Ring Opening ◽  
Halohydrin Dehalogenase

scholarly journals Cover Picture: Catalytic Promiscuity of Halohydrin Dehalogenase and its Application in Enantioselective Epoxide Ring Opening (ChemBioChem 7/2008)

ChemBioChem ◽  
2008 ◽  
Vol 9 (7) ◽  
pp. 1001-1001 ◽  
Author(s):  
Ghannia Hasnaoui-Dijoux ◽  
Maja Majerić Elenkov ◽  
Jeffrey H. Lutje Spelberg ◽  
Bernhard Hauer ◽  
Dick B. Janssen
Keyword(s):  
Ring Opening ◽  
Epoxide Ring ◽  
Catalytic Promiscuity ◽  
Epoxide Ring Opening ◽  
Halohydrin Dehalogenase

scholarly journals Two (Chemo)-Enzymatic Cascades for the Production of Opposite Enantiomers of Chiral Azidoalcohols

Catalysts ◽  
2021 ◽  
Vol 11 (8) ◽  
pp. 982
Author(s):  
Elia Calderini ◽  
Philipp Süss ◽  
Frank Hollmann ◽  
Rainer Wardenga ◽  
Anett Schallmey
Keyword(s):  
Ring Opening ◽  
Cascade Reactions ◽  
Second Step ◽  
Epoxide Ring ◽  
Reaction Intermediates ◽  
Halohydrin Dehalogenase ◽  
Enzymatic Cascades ◽  
Synthetic Routes ◽  
Molecular Complexity ◽  
Epoxidation Catalyst

Multi-step cascade reactions have gained increasing attention in the biocatalysis field in recent years. In particular, multi-enzymatic cascades can achieve high molecular complexity without workup of reaction intermediates thanks to the enzymes’ intrinsic selectivity; and where enzymes fall short, organo- or metal catalysts can further expand the range of possible synthetic routes. Here, we present two enantiocomplementary (chemo)-enzymatic cascades composed of either a styrene monooxygenase (StyAB) or the Shi epoxidation catalyst for enantioselective alkene epoxidation in the first step, coupled with a halohydrin dehalogenase (HHDH)-catalysed regioselective epoxide ring opening in the second step for the synthesis of chiral aliphatic non-terminal azidoalcohols. Through the controlled formation of two new stereocenters, corresponding azidoalcohol products could be obtained with high regioselectivity and excellent enantioselectivity (99% ee) in the StyAB-HHDH cascade, while product enantiomeric excesses in the Shi-HHDH cascade ranged between 56 and 61%.

Amino-functional polyethers: versatile, stimuli-responsive polymers

2020 ◽  
Vol 11 (24) ◽  
pp. 3940-3950 ◽  
Author(s):  
Patrick Verkoyen ◽  
Holger Frey
Keyword(s):  
Ring Opening ◽  
Review Article ◽  
Stimuli Responsive ◽  
New Class ◽  
Stimuli Responsive Polymers ◽  
Responsive Polymers

Amino-functional polyethers have emerged as a new class of “smart”, i.e. pH- and thermoresponsive materials. This review article summarizes the synthesis and applications of these materials, obtained from ring-opening of suitable epoxide monomers.

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