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First total synthesis of tubulysin B.
- Source :
-
Organic letters [Org Lett] 2009 Dec 17; Vol. 11 (24), pp. 5567-9. - Publication Year :
- 2009
-
Abstract
- The first total synthesis of tubulysin B is described. The aziridine route to tubuphenylalanine (Tup) of the tubulysin D/U-series could not be transferred to the synthesis of tubutyrosine (blue moiety). Therefore, tubutyrosine (Tut) was synthesized by a Wittig olefination/diastereoselective catalytic reduction sequence. Interestingly, the C-2 epimer of tubulysin B has a cytotoxic activity almost identical to the natural diastereomer.
- Subjects :
- Drug Screening Assays, Antitumor
Humans
Molecular Structure
Myxococcales chemistry
Oligopeptides chemistry
Oligopeptides pharmacology
Pipecolic Acids chemistry
Pipecolic Acids pharmacology
Stereoisomerism
Tubulin Modulators chemistry
Tubulin Modulators pharmacology
Oligopeptides chemical synthesis
Pipecolic Acids chemical synthesis
Tubulin Modulators chemical synthesis
Subjects
Details
- Language :
- English
- ISSN :
- 1523-7052
- Volume :
- 11
- Issue :
- 24
- Database :
- MEDLINE
- Journal :
- Organic letters
- Publication Type :
- Academic Journal
- Accession number :
- 19919080
- Full Text :
- https://doi.org/10.1021/ol902320w