Journal
CHEMICAL COMMUNICATIONS
Volume 52, Issue 26, Pages 4816-4819Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c6cc01428c
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Funding
- National Institute of General Medical Sciences of the NIH [GM-068649]
- NSF Graduate Research Fellowship Program
- Yale University Faculty of Arts and Sciences High Performance Computing Center
- NSF [CNS 08-21132]
- NATIONAL INSTITUTE OF GENERAL MEDICAL SCIENCES [R37GM068649, R01GM068649] Funding Source: NIH RePORTER
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We describe herein a crystallographic and NMR study of the secondary structural attributes of a beta-turn-containing tetra-peptide, Boc-Dmaa-D-Pro-Acpc-Leu-NMe2, which was recently reported as a highly effective catalyst in the atroposelective bromination of 3-arylquinazolin-4(3H)-ones. Inquiries pertaining to the functional consequences of residue substitutions led to the discovery of a more selective catalyst, Boc-Dmaa-D-Pro-Acpc-Leu-OMe, the structure of which was also explored. This new lead catalyst was found to exhibit a type I' beta-turn secondary structure both in the solid state and in solution, a structure that was shown to be an accessible conformation of the previously reported catalyst, as well.
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