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Synfacts 2020; 16(08): 0992
DOI: 10.1055/s-0040-1707445
Peptide Chemistry
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Fluorodehydroalanine-Containing Peptides

Contributor(s):
Hisashi Yamamoto
,
Tomohiro Hattori
Zhou H, van der Donk WA. * University of Illinois at Urbana-Champaign, USA
Synthesis of 2-Amino-3-fluoroacrylic Acid Containing Peptides.

Org. Lett. 2001;
3: 593-596
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Further Information

Publication History

Publication Date:
21 July 2020 (online)

 
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Key words

dehydroalanine - aminofluoroacrylates - fluoro-Pummerer rearrangement - fluorodehydroalanine

Significance

Dehydroalanine moieties occur abundantly as scaffolds in natural products. Also, fluorine-substituted compounds have received increasing attention due to their small steric bulk and their lipophilicity. The authors developed a strategy for the synthesis of fluorine-substituted dehydro­alanines.


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Comment

(E)- And (Z)-fluorodehydroalanines were synthesized from N-protected serines through a fluoro-Pummerer rearrangement. Moreover, this methodology can be applied in dipeptide synthesis.


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