Synthesis of the First α‐Fluoro‐Phosphotyrosyl Mimetic

References

• Welch , J. T. 1987 . Advances in the preparation of biologically active organofluorine compounds . Tetrahedron , 43 : 3123 – 3197 .
   Web of Science ®Google Scholar
• Burke , T. R. Jr. , Yao , Z.‐J. , Liu , D.‐G. , Voigt , J. and Gao , Y. 2001 . Phosphoryltyrosyl mimetics in the design of peptide‐based signal transduction inhibitors . Biopolymers , 60 : 32 – 44 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMedGoogle Scholar
• Burke , T. R. , Smyth , M. S. , Nomizu , M. , Otaka , A. and Roller , P. P. 1993 . Preparation of fluoro‐4‐(phosphonomethyl)‐D,L‐phenylalanine and hydroxy‐4‐(phosphonomethyl)‐D,L‐phenylalanine suitably protected for solid‐phase synthesis of p Peptides containing hydrolytically stable analogs of O‐phosphotyrosine . J. Org. Chem. , 58 : 1336 – 1340 .
   Web of Science ®Google Scholar
• Burke , T. R. , Liu , D. G. and Gao , Y. 2000 . Use of a Heck reaction for the synthesis of a new alpha‐azido phosphotyrosyl mimetic suitably protected for peptide synthesis . J. Org. Chem. , 65 : 6288 – 6291 . [PUBMED] [INFOTRIEVE] [CROSSREF]
   Google Scholar
• Marseigne , I. and Roques , B. P. 1988 . Synthesis of new amino acids mimicking sulfated and phosphorylated tyrosine residues . J. Org. Chem. , 53 : 3621 – 3624 .
   Google Scholar
• Burke , T. R. Jr. , Russ , P. and Lim , B. 1991 . Preparation of 4‐[bis(tert‐butyl)phosphonomethyl]‐N‐Fmoc‐DL‐phenylalanine; a hydrolytically stable analogue of O‐phosphotyrosine potentially suitable for peptide synthesis . Synthesis , 11 : 1019 – 1020 .
   Google Scholar
• Fritz‐Langhals , E. and Schutz , G. 1993 . Simple synthesis of optically active 2‐fluoroproprionic acid analogues of high enantiomeric purity . Tetrahedron Lett. , 34 : 293 – 296 . [CROSSREF]
   Google Scholar
• Evans , D. A. , Britton , T. C. , Ellman , J. A. and Dorow , R. L. 1990 . The asymmetric synthesis of α‐amino acids. Electrophilic azidation of chiral imide enolates, a practical approach to the synthesis of (R)‐ and (S)‐α‐azido carboxylic acids . J. Am. Chem. Soc. , 112 : 4011 – 4030 .
   Web of Science ®Google Scholar
• Davis , F. A. and Han , W. 1992 . Diastereoselective fluorination of chiral imide enolates using N‐fluoro‐O‐benzenedisulfonimide (NFOBS) . Tetrahedron Lett. , 33 : 1153 – 1156 . [CROSSREF]
   Web of Science ®Google Scholar
• Available from Sigma Aldrich Chemical Corp., Milwaukee, WI, USA
   Google Scholar
• Gao , Y. , Wei , C.‐Q. and Burke , T. R. Jr. 2001 . Olefin metathesis in the design and synthesis of a globally constrained Grb2 SH2 domain inhibitor . Org. Lett. , 3 : 1617 – 1620 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   Google Scholar
• Furet , P. , Gay , B. , Caravatti , G. , GarciaEcheverria , C. , Rahuel , J. , Schoepfer , J. and Fretz , H. 1998 . Structure‐based design and synthesis of high affinity tripeptide ligands of the Grb2‐SH2 domain . J. Med. Chem. , 41 : 3442 – 3449 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMedGoogle Scholar
• Yao , Z. J. , King , C. R. , Cao , T. , Kelley , J. , Milne , G. W.A. , Voigt , J. H. and Burke , T. R. 1999 . Potent inhibition of Grb2 SH2 domain binding by non‐phosphate‐containing ligands . J. Med. Chem. , 42 : 25 – 35 . [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   PubMed Web of Science ®Google Scholar
• Carpino , L. A. , Imazumi , H. , Foxman , B. M. , Vela , M. J. , Henklein , P. , El‐Faham , A. , Klose , J. and Bienert , M. 2000 . Comparison of the effects of 5‐ and 6‐HOAt on model peptide coupling reactions relative to the cases for the 4‐ and 7‐isomers . Org. Lett. , 2 : 2253 [PUBMED] [INFOTRIEVE] [CROSSREF] [CSA]
   Google Scholar
• Liu , D.‐G. , Yao , Z.‐J. , Gao , Y. and Burke , T. R. Jr. 2000 . Large scale preparation of cell permeable, non‐phosphate‐containing Grb2 SH2 domain inhibitors . Org. Prep. Proc. Int. , 32 : 197
   Web of Science ®Google Scholar