메뉴 건너뛰기




Volumn 34, Issue 21, 2004, Pages 3883-3889

Synthesis of the first α-fluoro-phosphotyrosyl mimetic

Author keywords

Chiral induction; Enantioselective; Fluorination; Phosphotyrosyl mimetic

Indexed keywords

2 FLUORO 4 [[BIS(1,1 DIMETHYLETHOXY)PHOSPHINYL]METHYL]BENZENEPROPANOIC ACID; 4 PHENYL 2 OXAZOLIDINONE; BENZENE DERIVATIVE; FLUORINE DERIVATIVE; OXAZOLIDINONE DERIVATIVE; PEPTIDE DERIVATIVE; PHOSPHOTYROSINE; PROPIONIC ACID DERIVATIVE; UNCLASSIFIED DRUG;

EID: 7644221986     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-200034770     Document Type: Article
Times cited : (7)

References (15)
  • 1
    • 0023237559 scopus 로고
    • Advances in the preparation of biologically active organofluorine compounds
    • Welch, J.T. Advances in the preparation of biologically active organofluorine compounds. Tetrahedron 1987, 43, 3123-3197.
    • (1987) Tetrahedron , vol.43 , pp. 3123-3197
    • Welch, J.T.1
  • 2
    • 0034957263 scopus 로고    scopus 로고
    • Phosphoryltyrosyl mimetics in the design of peptide-based signal transduction inhibitors
    • Burke, T.R., Jr.; Yao, Z.-J.; Liu, D.-G.; Voigt, J.; Gao, Y. Phosphoryltyrosyl mimetics in the design of peptide-based signal transduction inhibitors. Biopolymers 2001, 60, 32-44.
    • (2001) Biopolymers , vol.60 , pp. 32-44
    • Burke Jr., T.R.1    Yao, Z.-J.2    Liu, D.-G.3    Voigt, J.4    Gao, Y.5
  • 3
    • 0027231381 scopus 로고
    • 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
    • Burke, T.R.; Smyth, M.S.; Nomizu, M.; Otaka, A.; Roller, P.P. 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. 1993, 58, 1336-1340.
    • (1993) J. Org. Chem. , vol.58 , pp. 1336-1340
    • Burke, T.R.1    Smyth, M.S.2    Nomizu, M.3    Otaka, A.4    Roller, P.P.5
  • 4
    • 0342844295 scopus 로고    scopus 로고
    • Use of a Heck reaction for the synthesis of a new alpha-azido phosphotyrosyl mimetic suitably protected for peptide synthesis
    • Burke, T.R.; Liu, D.G.; Gao, Y. Use of a Heck reaction for the synthesis of a new alpha-azido phosphotyrosyl mimetic suitably protected for peptide synthesis. J. Org. Chem. 2000, 65, 6288-6291.
    • (2000) J. Org. Chem. , vol.65 , pp. 6288-6291
    • Burke, T.R.1    Liu, D.G.2    Gao, Y.3
  • 5
    • 0000489340 scopus 로고
    • Synthesis of new amino acids mimicking sulfated and phosphorylated tyrosine residues
    • Marseigne, I.; Roques, B.P. Synthesis of new amino acids mimicking sulfated and phosphorylated tyrosine residues. J. Org. Chem. 1988, 55, 3621-3624.
    • (1988) J. Org. Chem. , vol.55 , pp. 3621-3624
    • Marseigne, I.1    Roques, B.P.2
  • 6
    • 0026095904 scopus 로고
    • Preparation of 4-[bis(tert-butyl) phosphonomethyl]-N-Fmoc-DL- phenylalanine; a hydrolytically stable analogue of O-phosphotyrosine potentially suitable for peptide synthesis
    • Burke, T.R., Jr.; Russ, P.; Lim, B. Preparation of 4-[bis(tert-butyl) phosphonomethyl]-N-Fmoc-DL-phenylalanine; a hydrolytically stable analogue of O-phosphotyrosine potentially suitable for peptide synthesis. Synthesis 1991, 11, 1019-1020.
    • (1991) Synthesis , vol.11 , pp. 1019-1020
    • Burke Jr., T.R.1    Russ, P.2    Lim, B.3
  • 7
    • 0027532938 scopus 로고
    • Simple synthesis of optically active 2-fluoroproprionic acid analogues of high enantiomeric purity
    • Fritz-Langhals, E.; Schutz, G. Simple synthesis of optically active 2-fluoroproprionic acid analogues of high enantiomeric purity. Tetrahedron Lett. 1993, 34, 293-296.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 293-296
    • Fritz-Langhals, E.1    Schutz, G.2
  • 8
    • 0025324609 scopus 로고
    • 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
    • Evans, D.A.; Britton, T.C.; Ellman, J.A.; Dorow, R.L. 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. 1990, 112, 4011-4030.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 4011-4030
    • Evans, D.A.1    Britton, T.C.2    Ellman, J.A.3    Dorow, R.L.4
  • 9
    • 0026500332 scopus 로고
    • Diastereoselective fluorination of chiral imide enolates using N-fluoro-O-benzenedisulfonimide (NFOBS)
    • Davis, F.A.; Han, W. Diastereoselective fluorination of chiral imide enolates using N-fluoro-O-benzenedisulfonimide (NFOBS). Tetrahedron Lett. 1992, 33, 1153-1156.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 1153-1156
    • Davis, F.A.1    Han, W.2
  • 10
    • 7644224302 scopus 로고    scopus 로고
    • Available from Sigma Aldrich Chemical Corp., Milwaukee, WI, USA
    • Available from Sigma Aldrich Chemical Corp., Milwaukee, WI, USA.
  • 11
    • 0035979029 scopus 로고    scopus 로고
    • Olefin metathesis in the design and synthesis of a globally constrained Grb2 SH2 domain inhibitor
    • Gao, Y.; Wei, C.-Q.; Burke, T.R., Jr. Olefin metathesis in the design and synthesis of a globally constrained Grb2 SH2 domain inhibitor. Org. Lett. 2001, 3, 1617-1620.
    • (2001) Org. Lett. , vol.3 , pp. 1617-1620
    • Gao, Y.1    Wei, C.-Q.2    Burke Jr., T.R.3
  • 14
    • 0034720920 scopus 로고    scopus 로고
    • Comparison of the effects of 5- and 6-HOAt on model peptide coupling reactions relative to the cases for the 4- and 7-isomers
    • Carpino, L.A.; Imazumi, H.; Foxman, B.M.; Vela, M.J.; Henklein, P.; El-Faham, A.; Klose, J.; Bienert, M. 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. 2000, 2, 2253.
    • (2000) Org. Lett. , vol.2 , pp. 2253
    • Carpino, L.A.1    Imazumi, H.2    Foxman, B.M.3    Vela, M.J.4    Henklein, P.5    El-Faham, A.6    Klose, J.7    Bienert, M.8
  • 15
    • 0034341677 scopus 로고    scopus 로고
    • Large scale preparation of cell permeable, non-phosphate-containing Grb2 SH2 domain inhibitors
    • Liu, D.-G.; Yao, Z.-J.; Gao, Y.; Burke, T.R., Jr. Large scale preparation of cell permeable, non-phosphate-containing Grb2 SH2 domain inhibitors. Org. Prep. Proc. Int. 2000, 32, 197.
    • (2000) Org. Prep. Proc. Int. , vol.32 , pp. 197
    • Liu, D.-G.1    Yao, Z.-J.2    Gao, Y.3    Burke Jr., T.R.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.