Journal
TETRAHEDRON
Volume 67, Issue 35, Pages 6633-6643Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.05.073
Keywords
Argifin; Hydrophilic natural product; Chitinase inhibitor; Total synthesis; Hydrophobic tag; HO-TAGa; Solution-phase
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Funding
- Ministry of Education Culture, Sports, Science and Technology (MEXT)
- Grants-in-Aid for Scientific Research [21580129, 22790017] Funding Source: KAKEN
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A solution-phase total synthesis of argifin using 3,4,5-tris(octadecyloxy)benzyl tag as a hydrophobic protective group of carboxylic acid was developed to produce 44% overall yield for 16 linear steps. Argifin, a novel class of natural product chitinase inhibitor, is a highly water-soluble cyclic pentapeptide, so hitherto, only solid-phase synthesis techniques have been used to conveniently prepare the compound and its derivatives. 3,4,5-Tris(octadecyloxy)benzyl alcohol (HO-TAGa) and its esters are highly crystalline materials and highly capable of dissolving in less-polar solvents such as dichloromethane, benzene, THF, etc., but insoluble in polar solvents such as methanol and DMSO. The combination of HO-TAGa and Fmoc-based peptide synthesis, together with simple purification by recrystallization from MeOH solution, furnished an efficient and practical route of argifin production in the liquid-phase. (C) 2011 Elsevier Ltd. All rights reserved.
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