The cyclic dehydrodepsipeptide, AM-toxin II, was efficiently synthesized by a solid-phase method using a novel selenyl linker. The cleavage from the resin with formation of a double bond is successfully achieved under mild oxidative conditions with TBHP.
New selenyl linker for solid-phase synthesis of dehydropeptides
β Scribed by Kazuhiko Nakamura; Yuki Ohnishi; Eiji Horikawa; Takeo Konakahara; Masato Kodaka; Hiroaki Okuno
- Publisher
- Elsevier Science
- Year
- 2003
- Tongue
- French
- Weight
- 214 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
A novel linker possessing selenocyanate and masked carboxylic acid was developed for the solid-phase synthesis of dehydropeptides. This linker was used to demonstrate the synthesis of the model compound of RGD-conjugated dehydropeptide.
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The synthesis of 9-(4-hydroxyphenyl)-9-H-fluoren-9-ol and 5-(4-(9-hydroxy-9H-fluoren-9-yl)-phenoxy)pentanoic acid and their applications as new linkers for solid phase synthesis is reported. These supports show higher acid stability compared to standard trityl resins. Carboxylic acids and amines are
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