Efficient Biomimetic Total Synthesis, Characterization, and Antioxidant Activity of Ommatins.

ABSTRACT: Ommatins, natural colorants found in cephalopods and arthropods, are biosynthesized from tryptophan with uncyclized xanthommatin (Uc-Xa) as the key biosynthetic precursor. These pigments change color under oxidative or reductive conditions. Xanthommatin (Xa) and dihydro-xanthommatin (H₂-Xa), as well as decarboxylated xanthommatin (Dc-Xa) and decarboxylated-dihydro-xanthommatin (Dc-H₂-Xa), are some of the most common and well-studied ommatins. Herein, we describe the biomimetic total synthesis of Xa/H₂-Xa on a gram scale by using the Mannich reaction and oxidative dimerization as the key steps. The 7-step linear synthetic sequence achieved an overall yield of 27%. Dc-Xa/Dc-H₂-Xa and protected Uc-Xa/Uc-H₂-Xa were also synthesized from th

SUBMITTER: Huang L 

PROVIDER: S-EPMC11600184 | biostudies-literature | 2024 Nov

REPOSITORIES: biostudies-literature