Description and references

Naturally occurring family of macrocyclic peptides that inhibit serine proteases such as thrombin, q.v. Isolated from the Japanese marine sponge Theonella swinhoei; the two major forms, A and B, contain a vinylogous tyrosine (V-Tyr) and an α-ketoarginine residues - amino acids which were previously unknown in nature. Isoln and initial structure of A and B: N. Fusetani et al., J. Am. Chem. Soc. 112, 7053 (1990). Reassignment of stereochemistry and total synthesis of B: M. Hagihara, S. L. Schreiber, ibid. 114, 6570 (1992). Facile synthesis of B: H. M. M. Bastiaans et al., Tetrahedron Lett. 36, 5963 (1995). Isoln of C, D, E: Y. Nakao et al., Bioorg. Med. Chem. 3, 1115 (1995). Inhibition of thrombin and other serine proteases: S. D. Lewis et al., Thromb. Res. 70, 173 (1993). Molecular basis of inhibition and synthesis of A: B. E. Maryanoff et al., Proc. Natl. Acad. Sci. USA 90, 8048 (1993).

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Derivative