Synthesis of dolastatin 3

Details Synthesis of dolastatin 3 Synthesis of dolastatin 3

1988-10-24

1991-12-31

Lee, Lester L.

Chemistry: natural resins or derivatives; peptides or proteins;

Peptides of 3 to 100 amino acid residues

Synthesis of peptides

530317, 530330, C07K 304, C07K 512, C07K 764

Patent

active

050769731

ABSTRACT:
Synthesis of dolastatin 3 is accomplished by one amino acid unit addition from L-Pro-OMe employing diethyl phosphorocyanidate-triethylamine for peptide bond formation and N-Boc protection (trifluoroacetic acid cleavage). Thereafter Boc-L-Leu-L-(gln)Thz-(gly)Thz-L-Val-L-Pro-OMe was obtained, successively crystallized from ethanol-diethyl ether, converted to the OPfp active ester, Boc cleavage and cyclization in dioxane containing t-butanol and 4-pyrrolidinopyridine to yield synthetic (-)-dolastatin 3.

REFERENCES:
patent: 4291007 (1987-09-01), Dutta et al.
patent: 4882420 (1989-11-01), Thaisrivongs
patent: 4886813 (1989-12-01), Nakamura et al.
patent: 4898977 (1990-02-01), Herold et al.
Stewart et al. (1984) Solid Phase Peptide Synthesis (2d, ed) Laboratory Techniques in Solid Phase Peptide Synthesis, pp. 53-124.

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