Peptide-Like Molecules (PLMs): A Journey from Peptide Bond Isosteres to Gramicidin S Mimetics and Mitochondrial Targeting Agents
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چکیده
منابع مشابه
An evaluation of peptide-bond isosteres.
Peptide-bond isosteres can enable a deep interrogation of the structure and function of a peptide or protein by amplifying or attenuating particular chemical properties. In this Minireview, the electronic, structural, and conformational attributes of four such isosteres-thioamides, esters, alkenes, and fluoroalkenes-are examined in detail. In particular, the ability of these isosteres to partak...
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The design of peptide mimetic compounds is greatly facilitated by the identification of functionalities that can act as peptide replacements. The fluoroalkene moiety has recently been employed for that purpose. The purpose of this work is to examine the conformational ramifications of replacing peptide bonds with fluoroalkene moieties, thus generating peptidomimetics. The alanine dipeptide anal...
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To study the function of pantetheine in gramicidin S and tyrocidine biosynthesis, pepsin digests of the polymerizing enzymes, of which only the heavy ones contain pantetheine, were analyzed. The digests of gramicidin S enzymes charged with either [(14)C]proline or with D-phenylalanyl-[(14)C]proline, were analyzed by thin-layer chromatography; only the dipeptide showed a derivative associated wi...
متن کاملAntimicrobially active cycloundecapeptides related to gramicidin S having a novel turn structure with cis D-Phe-Pro peptide bond.
Antimicrobially active cycloundecapeptides related to gramicidin S, cyclo(-Val1-Orn2-Leu3-X4-D-Phe5-Pro6-Val7-Orn8- Leu9-D-Phe10-Pro11-) (X= Leu (1), Ala (2), Orn (3), Lys (4) and Arg (5)), were synthesized. From the CD and NMR studies, 1-5 possess antiparallel -sheet conformation linked by a type II -turn around D-Phe10-Pro11 and a novel turn structure around X4-D-Phe5-Pro6 sequence with cis D...
متن کاملNon-peptide linkages in gramicidin.
French, T. H., Hunter, G. D., Martin, A. J. P. & Popjik, G. (1951). Biochem. J. 48, vi. Graham, W. R. & Kay, H. D. (1934). J. Dairy Re8. 5, 54. Hawk, P. B., Oser, B. L. & Summerson, W. H. (1947). Practical Phy8iological Chemi8try, 12th ed. Philadelphia: Blakiston. Horecker, B. L., Ma, T. S. & Haas, E. (1940). J. biol. Chem. 136, 775. Houston, J., Kon, S. K. & Thompson, S. Y. (1940). J. Dairy Re...
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ژورنال
عنوان ژورنال: CHIMIA International Journal for Chemistry
سال: 2009
ISSN: 0009-4293
DOI: 10.2533/chimia.2009.764