Sandbox Reserved 1852: Difference between revisions
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==Introduction== | ==Introduction== | ||
[https://www.pnas.org/doi/full/10.1073/pnas.1401073111 Impact of Scaffold Rigidity] | [https://www.pnas.org/doi/full/10.1073/pnas.1401073111 Impact of Scaffold Rigidity] | ||
The Diels-Alderase protein aims to create optimal reacting conditions between the diene and dienophile in a [https://en.wikipedia.org/wiki/Diels%E2%80%93Alder_reaction Diels-Alder reaction.] It accomplishes this by decreasing the energy gap between the dienophile’s lowest unoccupied molecular orbital (LUMO) and the diene’s highest occupied molecular orbital (HOMO) in the transition state. The binding pocket of 4O5T is selective for two substrates, 4-carboxybenzyl trans-1,3-butadiene-1-carbamate (diene) and N,N- dimethylacrylamide (dienophile). The binding site contains an H-bond donor (Y134) which lowers the LUMO energy and stabilizes the negative charge on the dienophile and an H-bond acceptor (Q208) that increases the HOMO energy and stabilizes the positive charge on the diene. Both of these H-bonding interactions work to stabilize the transition state, while also orienting the substrates in optimal conformations for reacting. | The Diels-Alderase protein aims to create optimal reacting conditions between the diene and dienophile in a [https://en.wikipedia.org/wiki/Diels%E2%80%93Alder_reaction Diels-Alder reaction.] It accomplishes this by decreasing the energy gap between the dienophile’s lowest unoccupied molecular orbital (LUMO) and the diene’s highest occupied molecular orbital (HOMO) in the transition state.<ref name="Siegel">PMID:20647463</ref> The binding pocket of 4O5T is selective for two substrates, 4-carboxybenzyl trans-1,3-butadiene-1-carbamate (diene) and N,N- dimethylacrylamide (dienophile). The binding site contains an H-bond donor (Y134) which lowers the LUMO energy and stabilizes the negative charge on the dienophile and an H-bond acceptor (Q208) that increases the HOMO energy and stabilizes the positive charge on the diene. Both of these H-bonding interactions work to stabilize the transition state, while also orienting the substrates in optimal conformations for reacting. | ||
==General Structure== | ==General Structure== | ||
[[Image:BindingPocket.png|300px|right|thumb|Figure 1. Active Site]] | [[Image:BindingPocket.png|300px|right|thumb|Figure 1. Active Site]] | ||
