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Volumn 46, Issue 45, 2005, Pages 7733-7736

Semipermanent p-nitrobenzyloxycarbonyl (pNZ) protection of Orn and Lys side chains: Prevention of undesired α-Fmoc removal and application to the synthesis of cyclic peptides

Author keywords

Combinatorial chemistry; Orthogonal protecting group; Side reactions

Indexed keywords

CARBONYL DERIVATIVE; CYCLOPEPTIDE; ESTER DERIVATIVE; FLUORINE DERIVATIVE; LYSINE; NITROBENZENE DERIVATIVE; ORNITHINE;

EID: 26444472365     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.09.043     Document Type: Article
Times cited : (10)

References (30)
  • 7
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    • S.A. Kates F. Albericio Marcel Dekker New York, NY, USA
    • J.D. Wade S.A. Kates F. Albericio Solid-Phase Synthesis. A Practical Guide 2000 Marcel Dekker New York, NY, USA 103 128
    • (2000) Solid-Phase Synthesis. a Practical Guide , pp. 103-128
    • Wade, J.D.1
  • 11
    • 0003767945 scopus 로고    scopus 로고
    • S.A. Kates F. Albericio Marcel Dekker New York, NY, USA
    • P. Rovero S.A. Kates F. Albericio Solid-Phase Synthesis. A Practical Guide 2000 Marcel Dekker New York, NY, USA 331 364
    • (2000) Solid-Phase Synthesis. a Practical Guide , pp. 331-364
    • Rovero, P.1
  • 13
    • 0030934020 scopus 로고    scopus 로고
    • F. Guibé Tetrahedron 53 1997 13509 13556 and 1998, 54, 2967-3042
    • (1997) Tetrahedron , vol.53 , pp. 13509-13556
    • Guibé, F.1
  • 23
    • 10044234108 scopus 로고    scopus 로고
    • Fmoc-Orn(pNZ)-OH and Fmoc-Lys(pNZ)-OH were synthesized from Fmoc-Aaa(Boc)-OH and p-nitrobenzyl chloroformate as starting materials, by the azide method: L.J. Cruz, N.G. Beteta, A. Ewenson, and F. Albericio Org. Proc. Res. Dev. 8 2004 920 924
    • (2004) Org. Proc. Res. Dev. , vol.8 , pp. 920-924
    • Cruz, L.J.1    Beteta, N.G.2    Ewenson, A.3    Albericio, F.4
  • 26
    • 0032429560 scopus 로고    scopus 로고
    • The pNB group has been used to protect the C-terminal carboxylic group in side-chain or backbone anchoring strategies for the solid-phase synthesis of head-to-tail cyclic peptides. P. Romanovskis, and A.F. Spatola J. Pept. Res. 52 1998 356 374
    • (1998) J. Pept. Res. , vol.52 , pp. 356-374
    • Romanovskis, P.1    Spatola, A.F.2
  • 29
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    • note
    • tBu (1.68 g, 3 mmol) was dissolved in TFA/DCM (1:1) (20 mL) and stirred for 1 h. The solvent was then eliminated in vacuo and diethyl ether was added and evaporated four times in order to ensure that the TFA was removed. After drying the product in vacuo, a white solid was obtained (1.51 g, 3 mmol, nearly quantitative yield).


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