A Prebiotic Surface Catalysed Photochemically Activated Synthesis of L-Cysteine

DOI

10.2991/bep-16.2017.1How to use a DOI?

Keywords

ethyne; 2-amino ethenyl.porphin; 2-mercapto ethanimin-1yl porphin; l-cysteine

Abstract

Ethyne forms a weak charge-transfer complex with surface catalysts such as Mg.porphin in which the ethyne group has a net positive charge (0.08), and the conjugated porphin has a negative charge. This neutral complex is polarised and undergoes a nucleophilic addition reaction with ammonia at the carbene carbon to form Mg.2-amino ethenyl.porphin which has a tendency to the formation of cyclic Mg.1H aziridin-2yl.porphin complex. Nucleophilic attack by hydrosulfide anion ultimately yields a complex of bound 2-mercapto ethanimine. When the imine is bound to a Mg.porphin complex in which carbon monoxide has been oriented by exciting radiation an aziridine-2one complex is formed hydrolysable to the amino acid L-cysteine. The reactions have been shown to be feasible from the overall enthalpy changes in the ZKE approximation at the HF and MP2 /6-31G* level.

Copyright

© 2017, the Authors. Published by Atlantis Press.

Open Access

This is an open access article distributed under the CC BY-NC license (http://creativecommons.org/licenses/by-nc/4.0/).

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TY  - CONF
AU  - Nigel AYLWARD
PY  - 2016/12
DA  - 2016/12
TI  - A Prebiotic Surface Catalysed Photochemically Activated Synthesis of L-Cysteine
BT  - Proceedings of the 2016 International Conference on Biological Engineering and Pharmacy (BEP 2016)
PB  - Atlantis Press
SP  - 1
EP  - 5
SN  - 2468-5747
UR  - https://doi.org/10.2991/bep-16.2017.1
DO  - 10.2991/bep-16.2017.1
ID  - AYLWARD2016/12
ER  -