Stereoselective synthesis of α-monofluorinated phosphonate mimetics of naturally occurring phosphoserine and phosphothreonine, via electrophilic fluorination of lithiated bis-lactim ethersElectronic supplementary information (ESI) available: experimental data. See http://www.rsc.org/suppdata/cc/b2/b204093j/

Concepts

Natural SciencesChemistryMedicinal ChemistryOrganic ChemistrySynthetic Medicinal ChemistryOrganic SynthesisPeptide Bond ChemistryPeptide ChemistryPeptide Drug DiscoveryPeptidomimetic DesignExperimental Data CollectionFluorination ProcessesPeptidomimetic Library SynthesisSolid-phase Peptide SynthesisStereoselective SynthesisSynthetic Peptide Analogs

Abstract

Electrophilic fluorinations of lithiated bis-lactim ethers derived from cyclo-[L-AP4-D-Val] allow a direct access to alpha-monofluorinated phosphonate mimetics of naturally occurring phosphoserine and phosphothreonine, in enantiomerically pure form and suitably protected for solid-phase peptide synthesis.

References

Recent advances in electrophilic fluorination

Scott D. Taylor, Christopher C. Kotoris, Gabriel Hum · Tetrahedron · 1999 · 238 citations

Natural Sciences, Chemical Engineering, Chemistry +4

Nonhydrolyzable Phosphotyrosyl Mimetics for the Preparation Of Phosphatase-Resistant SH2 Domain Inhibitors

Terrence R. Burke, Mark S. Smyth, Motoyoshi Nomizu et al. · Biochemistry · 1994 · 196 citations

Life Sciences, Biochemistry, Pharmacology +17

Ready Access to Fluorinated Phosphonate Mimics of Secondary Phosphates. Synthesis of the (α,α-Difluoroalkyl)phosphonate Analogues of <scp>l</scp>-Phosphoserine, <scp>l</scp>-Phosphoallothreonine, and <scp>l</scp>-Phosphothreonine

David B. Berkowitz, MariJean Eggen, Quanrong Shen et al. · The Journal of Organic Chemistry · 1996 · 125 citations

Natural Sciences, Biochemistry, Chemistry +7

Synthesis of monofluoro- and difluoro- methylenephosphonate analogues of sn-glycerol-3-phosphate as substrates for glycerol-3-phosphate dehydrogenase and the X-ray structure of the fluoromethylenephosphonate moiety

Jens Nieschalk, Andrei S. Batsanov, David O’Hagan et al. · Tetrahedron · 1996 · 111 citations

Life Sciences, Biochemistry, Biology +9

α-Fluorinated Phosphonates as Substrate Mimics for Glucose 6-Phosphate Dehydrogenase: the CHF Stereochemistry Matters

David B. Berkowitz, Mohua Bose, Travis J. Pfannenstiel et al. · The Journal of Organic Chemistry · 2000 · 99 citations

Pharmacy, Biochemistry, Chemistry +7