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https://hdl.handle.net/2440/118413
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dc.contributor.author | Schumann, N.C. | - |
dc.contributor.author | Bruning, J. | - |
dc.contributor.author | Marshall, A.C. | - |
dc.contributor.author | Abell, A.D. | - |
dc.date.issued | 2019 | - |
dc.identifier.citation | Bioorganic and Medicinal Chemistry Letters, 2019; 29(3):396-399 | - |
dc.identifier.issn | 0960-894X | - |
dc.identifier.issn | 1464-3405 | - |
dc.identifier.uri | http://hdl.handle.net/2440/118413 | - |
dc.description.abstract | A series of dipeptide aldehydes containing different N-terminal heterocycles was prepared and assayed in vitro against α-chymotrypsin to ascertain the importance of the heterocycle in maintaining a β-strand geometry while also providing a hydrogen bond donor equivalent to the backbone amide nitrogen of the surrogate amino acid. The dipeptide containing a pyrrole constraint (10) was the most potent inhibitor, with >30-fold improved activity over dipeptides which lacked a nitrogen hydrogen bond donor (namely thiophene 11, furan 12 and pyridine 13). Molecular docking studies of 10 bound to α-chymotrypsin demonstrates a hydrogen bond between the pyrrole nitrogen donor and the backbone carbonyl of Gly216 located in the S3 pocket which is proposed to be critical for overall binding. | - |
dc.description.statementofresponsibility | Nicholas C.Schumann, John Bruning, Andrew C.Marshall, Andrew D.Abell | - |
dc.language.iso | en | - |
dc.publisher | Elsevier | - |
dc.rights | © 2018 Elsevier Ltd. All rights reserved. | - |
dc.source.uri | http://dx.doi.org/10.1016/j.bmcl.2018.12.032 | - |
dc.subject | Chymotrypsin | - |
dc.subject | Heterocycles | - |
dc.subject | Peptidic aldehydes | - |
dc.subject | Peptidomimetic | - |
dc.subject | Protease inhibitors | - |
dc.subject | β-Strand | - |
dc.title | The role of N-terminal heterocycles in hydrogen bonding to α-chymotrypsin | - |
dc.title.alternative | The role of N-terminal heterocycles in hydrogen bonding to alpha-chymotrypsin | - |
dc.type | Journal article | - |
dc.identifier.doi | 10.1016/j.bmcl.2018.12.032 | - |
dc.relation.grant | http://purl.org/au-research/grants/arc/CE140100003 | - |
pubs.publication-status | Published | - |
dc.identifier.orcid | Schumann, N.C. [0000-0002-6165-9066] | - |
dc.identifier.orcid | Bruning, J. [0000-0002-6919-1824] | - |
dc.identifier.orcid | Marshall, A.C. [0000-0002-9770-4594] | - |
dc.identifier.orcid | Abell, A.D. [0000-0002-0604-2629] | - |
Appears in Collections: | Aurora harvest 4 Physics publications |
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