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Leveraging Hydrazide as Protection for Carboxylic Acid: Suppression of Aspartimide Formation during Fmoc Solid-Phase Peptide Synthesis.
Sato, Kohei; Uemura, Haruna; Narumi, Tetsuo; Mase, Nobuyuki.
Afiliación
  • Sato K; Department of Engineering Graduate School of Integrated Science and Technology, Shizuoka University; 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan.
  • Uemura H; Department of Applied Chemistry and Biochemical Engineering Faculty of Engineering, Shizuoka University; 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan.
  • Narumi T; Graduate School of Science and Technology, Shizuoka University; 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan.
  • Mase N; Research Institute of Green Science and Technology, Shizuoka University; 3-5-1 Johoku, Hamamatsu, Shizuoka 432-8561, Japan.
Org Lett ; 26(21): 4497-4501, 2024 May 31.
Article en En | MEDLINE | ID: mdl-38768369
ABSTRACT
Despite numerous optimizations in peptide synthesis, the formation of aspartimide remains a significant side reaction that needs to be addressed. Herein, we introduce an approach that utilizes hydrazide as a carboxylic-acid-protecting group to reduce the formation of aspartimide. The aspartic acid hydrazide effectively suppressed the formation of aspartimide, even under microwave conditions, and was readily converted to native aspartic acid using CuSO4 in an aqueous medium.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Péptidos / Ácidos Carboxílicos / Ácido Aspártico / Técnicas de Síntesis en Fase Sólida Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Péptidos / Ácidos Carboxílicos / Ácido Aspártico / Técnicas de Síntesis en Fase Sólida Idioma: En Revista: Org Lett Asunto de la revista: BIOQUIMICA Año: 2024 Tipo del documento: Article País de afiliación: Japón Pais de publicación: Estados Unidos