5707-55-1Relevant articles and documents
Assessment of the in vitro and in vivo toxicity of 3,4- dihydroxyphenylacetaldehyde (DOPAL)
Bonnet,Legros,Janin,Dourmap,Costentin
, p. 323 - 331 (2004)
This work was carried out in order to evaluate the in vitro and in vivo toxicity of 3,4-dihydroxyphenylacetaldehyde (DOPAL). This aldehyde is formed from dopamine (DA) by monoamine oxidases (MAO) and is mainly oxidised to 3,4-dihydroxyphenylacetic acid by
The rearrangement of epinephrine.
FELLMAN
, p. 311 - 312 (1958)
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Transaminase-Mediated Amine Borrowing via Shuttle Biocatalysis
Taday, Freya,Ryan, James,O’Sullivan, Rachel,O’Reilly, Elaine
supporting information, p. 74 - 79 (2022/01/04)
Shuttle catalysis has emerged as a useful methodology for the reversible transfer of small functional groups, such as CO and HCN, and goes far beyond transfer hydrogenation chemistry. While a biocatalytic hydrogen-borrowing methodology is well established, the biocatalytic borrowing of alternative functional groups has not yet been realized. Herein, we present a new concept of amine borrowing via biocatalytic shuttle catalysis, which has no counterpart in chemo-shuttle catalysis and allows efficient intermolecular amine shuttling to generate reactive intermediates in situ. By coupling this dynamic exchange with an irreversible downstream step to displace the reaction equilibrium in the forward direction, high conversion to target products can be achieved. We showcase the potential of this amine-borrowing methodology using a biocatalytic equivalent of both the Knorr-pyrrole synthesis and Pictet-Spengler reaction.
Transaminase-Catalyzed Continuous Synthesis of Biogenic Aldehydes
Contente, Martina L.,Paradisi, Francesca
, p. 2830 - 2833 (2019/08/12)
The physiological role of biogenic aldehydes, such as 3,4-dihydroxyphenylacetaldehyde (DOPAL), has been associated with cardiovascular and neurodegenerative disorders. The availability of these substrates is limited and robust synthetic methodologies would greatly facilitate further biological studies. Herein, a transaminase-mediated single-step process in continuous mode, which leads to excellent product yields (90–95 %), is reported. Coimmobilization of the pyridoxal phosphate (PLP) cofactor eliminated the need for exogenous addition of this reagent without affecting the longevity of the system, delivering a truly self-sufficient process.
One-pot triangular chemoenzymatic cascades for the syntheses of chiral alkaloids from dopamine
Lichman,Lamming,Pesnot,Smith,Hailes,Ward
supporting information, p. 852 - 855 (2015/03/04)
We describe novel chemoenzymatic routes to (S)-benzylisoquinoline and (S)-tetrahydroprotoberberine alkaloids using the enzymes transaminase (TAm) and norcoclaurine synthase (NCS) in a one-pot, one-substrate 'triangular' cascade. Employment of up to two C-