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Sulfanylmethyldimethylaminopyridine as a Useful Thiol Additive for Ligation Chemistry in Peptide/Protein Synthesis.
Ohkawachi, Kento; Kobayashi, Daishiro; Morimoto, Kyohei; Shigenaga, Akira; Denda, Masaya; Yamatsugu, Kenzo; Kanai, Motomu; Otaka, Akira.
Afiliación
  • Ohkawachi K; Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan.
  • Kobayashi D; Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan.
  • Morimoto K; Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan.
  • Shigenaga A; Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan.
  • Denda M; Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan.
  • Yamatsugu K; Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
  • Kanai M; Graduate School of Pharmaceutical Sciences, The University of Tokyo, Tokyo 113-0033, Japan.
  • Otaka A; Institute of Biomedical Sciences and Graduate School of Pharmaceutical Sciences, Tokushima University, Tokushima 770-8505, Japan.
Org Lett ; 22(14): 5289-5293, 2020 07 17.
Article en En | MEDLINE | ID: mdl-32396369
ABSTRACT
Sulfanylmethyl-installed dimethylaminopyridine, 2-sulfanylmethyl-4-dimethylaminopyridine (2), has an acidic thiol group comparable to that in aryl thiols due to the formation of a zwitterion consisting of a thiolate anion and a pyridinium cation. It can be used as an additive for native chemical ligation. The alkyl thiol in 2 allows it to be used for the one-pot native chemical ligation-desulfurization protocol in peptide synthesis. The utility of 2 in the synthesis of cyclic peptides is demonstrated.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Péptidos Cíclicos / Piridinas / Compuestos de Sulfhidrilo / Proteínas / Técnicas de Química Sintética Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Japón
Texto completo
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Péptidos Cíclicos / Piridinas / Compuestos de Sulfhidrilo / Proteínas / Técnicas de Química Sintética Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2020 Tipo del documento: Article País de afiliación: Japón