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Synfacts 2025; 21(01): 99
DOI: 10.1055/a-2467-5807
Peptide Chemistry

Synthesis of (2S,3R,4R)-Dihydroxyisoleucine (DHIle) and Its Application in Amatoxin Synthesis

Contributor(s):
Hisashi Yamamoto
,
Abhijit Paul 
Chandra SD, Gunasekara S, Noichl BP, Patrick BO, Perrin DM *. University of British Columbia, Vancouver, Canada
Synthesis of (2S,3R,4R)-Dihydroxyisoleucine for Use in Amatoxin Synthesis.

J. Org. Chem. 2024;
89: 12739-12747
DOI: 10.1021/acs.joc.4c01051
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Keywords

dihydroxy isoleucine - metal free - high selectivity - amanitin - amatoxin

Significance

The amatoxin analogue 1 is used as a cytotoxic agent in cancer research. The authors developed the synthesis of DHIle, an amino acid found in α-amanitin. This method is metal-free and enables significant DHIle production with suitable protection for peptides.


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Comment

A new method for synthesizing DHIle has been devised, eliminating the use of hazardous metals, reactive reagents, carbon-intensive N-protection, and cyanide in large-scale Strecker reactions. This technique is the most efficient chemical synthesis of protected DHIle to date.


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Publication History

Article published online:
20 December 2024

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