Abstract
A previously synthesized unit of dolastatin 10 (1), dolaphenine (Doe, 3), was converted in four steps to tripeptide 10. Subsequent condensation with carboxylic acid 11 (four steps from Meldrum's acid) provided a practical synthesis of the cancer cell growth inhibitor dolastatin 18 (2, Dhex-(S)-Leu-(R)-N-Me-Phe-Doe). The synthesis of dolastatin 18 (2) confirmed the R stereochemistry of the N-Me-Phe unit as originally assigned and unusual among amino acid components of the sea hare Dolabella auricularia. An X-ray crystal structure determination of dolastatin 18 was also completed.
Original language | English (US) |
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Pages (from-to) | 4019-4022 |
Number of pages | 4 |
Journal | Journal of Organic Chemistry |
Volume | 69 |
Issue number | 12 |
DOIs | |
State | Published - Jun 11 2004 |
ASJC Scopus subject areas
- Organic Chemistry
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Dive into the research topics of 'Synthesis and X-ray crystal structure of the Dolabella auricularia peptide dolastatin 18'. Together they form a unique fingerprint.Datasets
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CCDC 245629: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Hogan, F. (Creator), Herald, D. L. (Creator) & Pettit, G. R. (Creator), The Cambridge Structural Database, 2004
DOI: 10.5517/cc87ljl, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc87ljl&sid=DataCite
Dataset
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CCDC 245628: Experimental Crystal Structure Determination
Pettit, G. R. (Creator), Hogan, F. (Creator), Herald, D. L. (Creator) & Pettit, G. R. (Creator), The Cambridge Structural Database, 2004
DOI: 10.5517/cc87lhk, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc87lhk&sid=DataCite
Dataset