Synthesis of protected L-4-[sulfono(difluoromethyl)]phenylalanine and its incorporation into a peptide

Authors
Liu, SF Dockendorff, C Taylor, SD
Citation
Sf. Liu et al., Synthesis of protected L-4-[sulfono(difluoromethyl)]phenylalanine and its incorporation into a peptide, ORG LETT, 3(10), 2001, pp. 1571-1574
Citations number
21
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ORGANIC LETTERS
ISSN journal
15237060 → ACNP
Volume
3
Issue
10
Year of publication
2001
Pages
1571 - 1574
Database
ISI
SICI code
1523-7060(20010517)3:10<1571:SOPLAI>2.0.ZU;2-N
Abstract
[GRAPHICS] A protected form of L-4-[sulfono(difluoromethyl)]phenylalanine (F(2)Smp), a novel non hydrolyzable phospho- and sulfotyrosine mimetic, was synthesized via electrophilic fluorination of a benzylic sulfonate followed by a Pd-ca talyzed cross coupling reaction between the fluorinated sulfonate and the z incate of protected iodoalanine, F(2)Smp was incorporated into a peptide us ing solid-phase peptide synthesis techniques.