Structural Formula Vector Image
Title: Cyclotheonamides
Literature 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 a-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).
Derivative Type: Cyclotheonamide A
CAS Registry Number: 129033-04-1
CAS Name: [S(E)]-3-[[4-Amino-5-(4-hydroxyphenyl)-1-oxo-2-pentenyl]amino]-N-formyl-L-alanyl-L-prolyl-N6-(aminoiminomethyl)-2-oxo-L-3,6-diaminohexanoyl-D-phenylalanine cyclic (4®1)-peptide
Manufacturers' Codes: MS-1144
Molecular Formula: C36H45N9O8
Molecular Weight: 731.80
Percent Composition: C 59.09%, H 6.20%, N 17.23%, O 17.49%
Properties: uv max (methanol): 278 nm (e 1940). [a]D23 -13° (c = 0.2 in methanol).
Optical Rotation: [a]D23 -13° (c = 0.2 in methanol)
Absorption maximum: uv max (methanol): 278 nm (e 1940)
Derivative Type: Cyclotheonamide B
CAS Registry Number: 129033-05-2
Molecular Formula: C37H47N9O8
Molecular Weight: 745.82
Percent Composition: C 59.58%, H 6.35%, N 16.90%, O 17.16%
Properties: [a]D23 -13.5° (c = 0.2 in methanol).
Optical Rotation: [a]D23 -13.5° (c = 0.2 in methanol)

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