223526-27-0Relevant articles and documents
An improved synthesis of (2S, 4S)- and (2S, 4R)-2-amino-4-methyldecanoic acids: Assignment of the stereochemistry of culicinins
Zhang, Wei,Ding, Ning,Li, Yingxia
, p. 576 - 580 (2012/06/01)
An improved synthesis of (2S, 4S)- and (2S, 4R)-2-amino-4-methyldecanoic acids was accomplished using a glutamate derivative as starting material and Evans' asymmetric alkylation as the decisive step. The NMR data of the two diastereomers were measured and compared with those of the natural product. As a result, the stereochemistry of this novel amino acid unit in culicinins was assigned as (2S, 4R).
Structure-based design, synthesis, and biological evaluation of irreversible human rhinovirus 3C protease inhibitors. 4. Incorporation of P1 lactam moieties as L-glutamine replacements
Dragovich, Peter S.,Prins, Thomas J.,Zhou, Ru,Webber, Stephen E.,Marakovits, Joseph T.,Fuhrman, Shella A.,Patick, Amy K.,Matthews, David A.,Lee, Caroline A.,Ford, Clifford E.,Burke, Benjamin J.,Rejto, Paul A.,Hendrickson, Thomas F.,Tuntland, Tove,Brown, Edward L.,Meador III, James W.,Ferre, Rose Ann,Harr, James E. V.,Kosa, Maha B.,Worland, Stephen T.
, p. 1213 - 1224 (2007/10/03)
The structure-based design, chemical synthesis, and biological evaluation of various human rhinovirus (HRV) 3C protease (3CP) inhibitors which incorporate P1 lactam moieties in lieu of an L-glutamine residue are described. These compounds are comprised of a tripeptidyl or peptidomimetic binding determinant and an ethyl propenoate Michael acceptor moiety which forms an irreversible covalent adduct with the active site cysteine residue of the 3C enzyme. The P1-lactam-containing inhibitors display significantly increased 3CP inhibition activity along with improved antirhinoviral properties relative to corresponding L-glutamine-derived molecules. In addition, several lactam-containing compounds exhibit excellent selectivity for HRV 3CP over several other serine and cysteine proteases and are not appreciably degraded by a variety of biological agents. One of the most potent inhibitors (AG7088, mean antirhinoviral EC90 ? 0.10 μM, n = 46 serotypes) is shown to warrant additional preclinical development to explore its potential for use as an antirhinoviral agent.
