An exceptionally mild and efficient route to dehydroalanine peptides

Journal of the Chemical Society, Chemical Communications

Volumn , Issue 16, 1992, Pages 1145-1147

  Ranganathan, Darshan ^a   Shah, Kavita ^a   Vaish, Narendra ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY KANPUR   (India)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 37049071365     PISSN: 00224936     EISSN: None     Source Type: Journal    
DOI: 10.1039/C39920001145     Document Type: Article

References (12)

1. Dehydroamino acids have been found to occur in biologically active metabolites of bacterial, fungal and marine origin, U., Schmidt, E., Ohlev, J., Hausler, H., Poisel, W., Herz, H., Grisebach and G. W., Kirby, Progress in the Chemistry of Organic Natural Products, Springer-Verlag, Wien, 1979, vol. 37, p. 251–327
2. C. H., Stammer, in Chemistry and Biochemistry of Amino Acids, Peptides and Proteins, Marcell Dekker Inc., New York, 1982, vol. 6, pp. 33–74
3. K., Noda, Y., Shimohigashi and N., Izumiya, in The Peptides, vol. 5, Academic Press, New York, 1983, p. 285
4. U., Schmidt, A., Lieberknecht, J., Wild, Synthesis, 1988, 3, 159
5. The presence of these residues has been shown to impart enhanced resistance to enzymatic degradation, M. L., English, C. H., Stammer, Biochem. Biophys. Res. Commun., 1978, 83, 1464
6. The unique conformational features of dehydro peptides have attracted considerable attention in recent years. There is evidence that the introduction of these units into peptide sequences induces folding of the backbone to give β-bends.M. R., Ciazolo, A., Tuzi, C. R., Pratesi, A., Fissi, O., Pieroni, Biopolymers, 1990, 30, 911
7. O., Pieroni, A., Fissi, C., Pratesi, P. A., Temussi, F., Ciardelli, J. Am. Chem. Soc., 1991, 113, 6338Recent studies have shown that the biosynthesis of mono sulfide bridges in peptide metabolites involves the stereospecific addition of cysteine thiol groups to Δ-Ala residues. Such motifs are a characteristic feature of lantibiotics, an important class of antibiotics of fungal origin and exemplified with nisin (a food preservative), epidermin (a therapeutic agent against acne). ancovenin, duramycin (immunoactive agents) and mersacidin, actergardine (antibiotics)
8. G., Jung, Angew. Chem., Int. Ed. Engl., 1991, 30, 1051
9. D., Ranganathan, S., Saini, J. Am. Chem. Soc., 1991, 113, 1042
10. The α-keto amide unit (–NH–CO–CO–), present in the powerful immunosuppressants rapamycin, FK-506 and related antibiotics, has recently been identified as the key structural element inovolved in direct binding with immunophilin proteins (rotamases) leading to the inhibition of their prolyl cis→trans isomerase activity, S. L., Schreiber, Science, 1991, 251, 283
11. G. D., Van Duyne, R. F., Standaert, S. L., Schreiber, J., Clardy, J. Am. Chem. Soc., 1991, 113, 7433
12. D., Ranganathan, K., Shah and N., Vaish, unpublished results.