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First total synthesis and biological evaluation of the cyclic heptapeptide rhizonin A

✍ Scribed by Hiroshi Nakatsuka; Kenichiro Shimokawa; Ryoka Miwa; Kaoru Yamada; Daisuke Uemura

Book ID: 104095985
Publisher: Elsevier Science
Year: 2009
Tongue: French
Weight: 205 KB
Volume: 50
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.10.124

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✦ Synopsis

The first total synthesis and biological evaluation of the naturally occurring cyclic heptapeptide rhizonin A are described. The synthesis includes solution-phase peptide synthesis and the preparation of NMe-3-(3-furyl)alanine (NMe-FurAla), a unique component of rhizonin A, which was prepared in chiral form via Barton-MacCombie deoxygenation as a key step. The bioactivity was assessed using 3T3-L1 murine adipocytes.

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