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약학대학
약학과
Journal papers
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Synthesis of a cyclic analogue of Tuv N-methyl tubulysin
Title
Synthesis of a cyclic analogue of Tuv N-methyl tubulysin
Authors
Park Y.
;
Lee J.K.
;
Ryu J.-S.
Ewha Authors
류재상
SCOPUS Author ID
류재상
Issue Date
2015
Journal Title
Synlett
ISSN
9365-5214
Citation
Synlett vol. 26, no. 8, pp. 1063 - 1068
Keywords
antitumor agents
;
asymmetric catalysis
;
asymmetric synthesis
;
Diels-Alder reaction
;
medicinal chemistry
;
peptides
Publisher
Georg Thieme Verlag
Indexed
SCI; SCIE; SCOPUS
Document Type
Article
Abstract
Abstract Tubulysins are the most potent antimitotic agents known so far. We are interested in the conformational effect of tubulysin and herein we report the design and synthesis of a conformationally rigid cyclic analogue of Tuv N-methyl tubulysin. A conformationally rigid tetrahydropyran moiety was incorporated into the Tuv fragment via enantioselective hetero Diels-Alder reaction to prevent the rotation of the Tuv chain. The following diastereoselective reductive amination yielded the (4-methylamino)tetrahydropyranyl Tuv fragment, which was coupled to d-Mep-l-Ile dipeptide fragment and Tup fragment sequentially. © Georg Thieme Verlag.
DOI
10.1055/s-0034-1379900
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