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Volumn 40, Issue 40, 1999, Pages 7279-7282

Selective solid-phase iodination of phenolic groups with bis(pyridine)iodonium (I) tetrafluoroborate

Author keywords

Biologically active compounds; Halogenation; Protecting groups; Supported reagents reactions

Indexed keywords

DERMORPHIN; ETHER DERIVATIVE; ORGANOIODINE DERIVATIVE; ORGANOSILICON DERIVATIVE; PHENOL DERIVATIVE;

EID: 0033215052     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01522-1     Document Type: Article
Times cited : (11)

References (24)
  • 1
    • 0001186913 scopus 로고
    • Abel, E. W.; Stone, F. G.-A.; Wilkinson, G., Eds.Pergamon Press: Oxford
    • For a recent review, see: Farina, V. In Comprehensive Organometallic Chemistry II; Abel, E. W.; Stone, F. G.-A.; Wilkinson, G., Eds.Pergamon Press: Oxford, 1995; Vol. 12; pp. 161-240.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 161-240
    • Farina, V.1
  • 8
    • 0033515798 scopus 로고    scopus 로고
    • Iodinated phenols obtained by this procedure can be further functionalized to give derivatives with pharmacological activity. One recent example is the synthesis of C-methylated phenols using the iodonium reagent: Turnbull, K. D.; Hudgens, T. L. Tetrahedron Lett. 1999, 40, 2719-2722.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 2719-2722
    • Turnbull, K.D.1    Hudgens, T.L.2
  • 14
    • 0026446220 scopus 로고
    • The TBDMS group is a common protecting group for the the hydroxyl found in the side chain of Ser, Thr and Tyr, used in the global phosphorylation peptide approach. FmocTyr(OTBDMS)OH was prepared following described procedure, see: Fischer, P. M. Tetrahedron Lett. 1992, 33, 7605-7608.
    • (1992) Tetrahedron Lett. , vol.33 , pp. 7605-7608
    • Fischer, P.M.1
  • 15
    • 0009702443 scopus 로고    scopus 로고
    • note
    • 2 at room temperature, for 10 min. In the solid phase, a rink amide resin was chosen because of the simplicity to anchor amino acids to the resin through an amide linkage (standard solid-phase protocols).
  • 17
    • 1842291024 scopus 로고    scopus 로고
    • Radioiodinated analogues of dermorphin were prepared by incorporating new reactive groups in the C-terminal part of the sequence and then introducing iodine on these groups: Gaudriault, G.; Zürger, N.; Vicent, J. P. J. Neurochem. 1997, 68, 813-819.
    • (1997) J. Neurochem. , vol.68 , pp. 813-819
    • Gaudriault, G.1    Zürger, N.2    Vicent, J.P.3
  • 18
    • 0009677536 scopus 로고    scopus 로고
    • note
    • 3SiH =95:2.5:2.5).
  • 19
    • 0009734561 scopus 로고    scopus 로고
    • 2
    • 2.
  • 20
    • 0009680031 scopus 로고    scopus 로고
    • 1H-NMR, thus confirming the observation that protected Tyr residues are unreactive
    • 1H-NMR, thus confirming the observation that protected Tyr residues are unreactive.
  • 21
    • 0009744438 scopus 로고    scopus 로고
    • Identified by comparison with a commercial sample of dermorphin
    • Identified by comparison with a commercial sample of dermorphin.
  • 22
    • 0009734562 scopus 로고    scopus 로고
    • As for example the di-iodinated dermorphin analogue 8 was also prepared by iodination of the two monoprotected Tyr peptidyl resins (1 and 2) and cleavage of the corresponding di-iodinated resins 1I and 2I
    • As for example the di-iodinated dermorphin analogue 8 was also prepared by iodination of the two monoprotected Tyr peptidyl resins (1 and 2) and cleavage of the corresponding di-iodinated resins 1I and 2I.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.