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.
Design and Use of de novo Cascades for the Biosynthesis of New Benzylisoquinoline Alkaloids
Wang, Yu,Tappertzhofen, Nadine,Méndez-Sánchez, Daniel,Bawn, Maria,Lyu, Boyu,Ward, John M.,Hailes, Helen C.
, p. 10120 - 10125 (2019/06/27)
The benzylisoquinoline alkaloids (BIAs) are an important group of secondary metabolites from higher plants and have been reported to show significant biological activities. The production of BIAs through synthetic biology approaches provides a higher-yielding strategy than traditional synthetic methods or isolation from plant material. However, the reconstruction of BIA pathways in microorganisms by combining heterologous enzymes can also give access to BIAs through cascade reactions. Most importantly, non-natural BIAs can be generated through such artificial pathways. In the current study, we describe the use of tyrosinases and decarboxylases and combine these with a transaminase enzyme and norcoclaurine synthase for the efficient synthesis of several BIAs, including six non-natural alkaloids, in cascades from l-tyrosine and analogues.
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-