期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 77, 期 23, 页码 10596-10616出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo3017499
关键词
-
资金
- University of New South Wales Sydney
- Frasch foundation [658-HF07]
We report the first synthesis of sanguinamide B analogues. Substituting N-methylated (N-Me) amino acids, glycine (Gly), and L- or D-phenylalanine (Phe) into the backbone of sanguinamide B showed that only L- and D-Phe residues controlled the macrocycle conformation. The N-methylated and glycine analogues all had multiple conformations, whereas the L- and D-Phe derivatives only had a single conformation. Testing of all conformer analogues showed that inclusion of an L- or D-Phe was a superior design element than incorporating the N-Me moiety that is often utilized to control macrocyclic conformation. Finally, we show that there is an ideal Phe residue (in this case L-Phe) for generating compounds that have the greatest inhibitory effect on bacterial motility. Our data support the hypothesis that the macrocyclic conformation is dictated by the benzyl moiety requiring a pseudoequatorial position, and all other energy considerations are secondary.
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