Stereoselective Oxidation of Aryl-Substituted Vicinal Diols into Chiral α-Hydroxy Aldehydes by Re-Engineered Propanediol Oxidoreductase

ACS Catalysis ◽  
2013 ◽  
Vol 3 (12) ◽  
pp. 3016-3025 ◽  
Author(s):  
Cecilia Blikstad ◽  
Käthe M. Dahlström ◽  
Tiina A. Salminen ◽  
Mikael Widersten
Keyword(s):  
Vicinal Diols ◽  
Hydroxy Aldehydes ◽  
Stereoselective Oxidation

Imine Based Self-Healing Hydrogel Triggered by Periodate

2020 ◽  
Author(s):  
Alexis Wolfel ◽  
Cecilia Inés Alvarez Igarzabal ◽  
Marcelo Ricardo Romero
Keyword(s):  
Functional Groups ◽  
Time Window ◽  
Crosslinking Reaction ◽  
Self Healing ◽  
Swelling Properties ◽  
Covalent Bonds ◽  
Smart Systems ◽  
Primary Amino ◽  
Vicinal Diols ◽  
Aldehyde Groups

<p>Design of materials with novel sensitivities and smart behaviour is important for the development of smart systems with automated responsiveness. We have recently reported the synthesis of hydrogels, cross-linked by <i>N,N'</i>-diallyltartardiamide (DAT). The covalent DAT-crosslinking points have vicinal diols which can be easily cleaved with periodate, generating valuable a-oxo-aldehyde functional groups, useful for further chemical modification. Based on those findings, we envisioned that a self-healable hydrogel could be obtained by incorporation of primary amino functional groups, from <a>2-aminoethyl methacrylate </a>hydrochloride (AEMA), coexisting with DAT into the same network. The a-oxo-aldehyde groups generated after the reaction with periodate would arise in the immediate environment of amine groups to form imine cross-links. For this purpose, DAT-crosslinked hydrogels were synthesized and carefully characterized. The cleavage of DAT-crosslinks with periodate promoted changes in the mechanical and swelling properties of the materials. As expected, a self-healing behavior was observed, based on the spontaneous formation of imine covalent bonds. In addition, we surprisingly found a combination of fast vicinal diols cleavage and a low speed self-crosslinking reaction by imine formation. Consequently, it was found a time-window in which a periodate-treated polymer was obtained in a transient liquid state, which can be exploited to choose the final shape of the material, before automated gelling. The singular properties attained on these hydrogels could be useful for developing sensors, actuators, among other smart systems.</p>

Chemo-, Regio-, and Stereoselective Oxidation of the Monocyclic Diterpenoid β-Cembrenediol by P450 BM3

ACS Catalysis ◽  
2015 ◽  
Vol 5 (3) ◽  
pp. 1772-1780 ◽  
Author(s):  
Priska Le-Huu ◽  
Tanja Heidt ◽  
Birgit Claasen ◽  
Sabine Laschat ◽  
Vlada B. Urlacher
Keyword(s):  
P450 Bm3 ◽  
Stereoselective Oxidation

Catalytic oxidation of vicinal diols to .alpha. diketones

1972 ◽  
Vol 37 (11) ◽  
pp. 1832-1833 ◽  
Author(s):  
Steven L. Regen ◽  
George M. Whitesides
Keyword(s):  
Catalytic Oxidation ◽  
Vicinal Diols

New allylstannanes for the connective construction of monoprotected vicinal diols

1987 ◽  
Vol 28 (2) ◽  
pp. 139-142 ◽  
Author(s):  
Gary E Keck ◽  
Duain E Abbott ◽  
Michael R Wiley
Keyword(s):  
Vicinal Diols

Efficient synthesis of quinoxalines from 2-nitroanilines and vicinal diols via a ruthenium-catalyzed hydrogen transfer strategy

2015 ◽  
Vol 17 (1) ◽  
pp. 279-284 ◽  
Author(s):  
Feng Xie ◽  
Min Zhang ◽  
Huanfeng Jiang ◽  
Mengmeng Chen ◽  
Wan Lv ◽  
...  
Keyword(s):  
Hydrogen Transfer ◽  
Efficient Synthesis ◽  
Vicinal Diols

An efficient synthesis of quinoxalines from 2-nitroanilines and biomass-derived vicinal diols is demonstrated via a hydrogen transfer strategy.

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