期刊
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
卷 139, 期 14, 页码 5233-5241出版社
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b01624
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资金
- Bristol-Myers Squibb
- NIH [F32GM117816, GM-118176]
- NSF GRFP
A thermodynamic approach to peptide macrocyclization inspired by the cyclization of non-ribosomal peptide aldehydes is presented. The method provides access to structurally diverse macro cycles by exploiting the reactivity of transient macrocyclic peptide imines toward inter- and intramolecular nucleophiles. Reactions are performed in aqueous media, in the absence of side chain protecting groups, and are tolerant of all proteinogenic functional groups. Macrocyclic products bearing non-native and rigidifying structural motifs, isotopic labels, and a variety of bioorthogonal handles are prepared, along with analogues of four distinct natural products. Structural interrogation of the linear and macrocyclic peptides using variable-temperature NMR and circular dichroism suggests that preorganization of linear substrates is not a prerequisite for macrocyclization.
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