title: Synthesis of stereochemically diverse cyclic analogs of tubulysins.
abstract: The synthesis of tubulysin analogs containing stereochemically diverse cyclic Tuv moieties is described. A tetrahydropyranyl moiety was incorporated into the Tuv unit by enantioselective hetero Diels-Alder reactions of Danishefsky's diene and thiazole aldehyde. Four different stereoisomers of cyclic Tuv units were used as surrogates for the Tuv moiety. The synthesized stereochemically diverse simplified cyclic analogs were evaluated for the inhibition of tubulin polymerization.
authors.affiliation: College of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52, Ewhayeodae-gil, Seodaemun-gu, Seoul 03760, Republic of Korea.
authors.forename: Yunjeong
authors.initials: Y
authors.lastname: Park
authors.affiliation: College of Pharmacy, Seoul National University, Seoul 151-742, Republic of Korea.
authors.forename: Song Yi
authors.initials: SY
authors.lastname: Bae
authors.affiliation: Department of Pharmacy, College of Pharmacy, Institute of Pharmaceutical Science and Technology, Hanyang University, 55, Hanyangdaehak-ro, Sangnok-gu, Ansan, Kyeonggi-do 426-791, Republic of Korea.
authors.forename: Jung-Mi
authors.initials: JM
authors.lastname: Hah
authors.affiliation: College of Pharmacy, Seoul National University, Seoul 151-742, Republic of Korea. Electronic address: sklee61@snu.ac.kr.
authors.forename: Sang Kook
authors.initials: SK
authors.lastname: Lee
authors.affiliation: College of Pharmacy & Graduate School of Pharmaceutical Sciences, Ewha Womans University, 52, Ewhayeodae-gil, Seodaemun-gu, Seoul 03760, Republic of Korea. Electronic address: ryuj@ewha.ac.kr.
authors.forename: Jae-Sang
authors.initials: JS
authors.lastname: Ryu
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000378:metabolism; D002384:Catalysis; D061565:Cycloaddition Reaction; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000378:metabolism; D013237:Stereoisomerism; D014404:Tubulin / Q000737:chemistry / Q000378:metabolism
chemical_list: D000970:Antineoplastic Agents; D009842:Oligopeptides; D014404:Tubulin
keywords: Antitumor agents; Asymmetric catalysis; Hetero Diels–Alder reaction; Peptides; Tubulysin