Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000084.xml
Synthesis 2002(1): 0126-0132
DOI: 10.1055/s-2002-19311
DOI: 10.1055/s-2002-19311
PAPER
© Georg Thieme Verlag Stuttgart · New York
Di-, Tri- and Tetrapeptide-Linked Dicatechol Derivatives
Further Information
Received
25 August 2001
Publication Date:
04 August 2004 (online)
Publication History
Publication Date:
04 August 2004 (online)
Abstract
Di-, tri- and tetrapeptide linked dicatechol derivatives are prepared by subsequent coupling of 2,3-dimethoxybenzoic acid (2), peptides 3 and 2,3-dimethoxybenzylamine (5) using classical activating conditions (EDC/HOBt or DDC/HOSu). In the final step the methyl ethers at the veratrol units are cleaved to afford the free catechol derivatives 7, which are potential ligands for metal complexes with well defined fixed conformations at the peptide spacers.
Key words
amides - peptides - ligands - supramolecular chemistry
-
1a
Creighton TE. Proteins, Structures and Molecular Properties W. H. Freeman; New York: 1984. -
1b
Fersht A. Structure and Mechanism in Protein Science W. H. Freeman; New York: 1998. -
2a
Lippard SJ.Berg JM. Principles in Bioinorganic Chemistry University Science Books; Mill Valey: 1994. -
2b
Sträter N.Lipscomb WN.Klabunde T.Krebs B. Angew. Chem. Int. Ed. Engl. 1996, 35: 2024 , Angew. Chem. 1996, 108, 2158 -
2c
Schneider JP.Kelly JW. J. Am. Chem. Soc. 1995, 117: 2533 -
2d
Ghadiri MR. J. Am. Chem. Soc. 1992, 114: 825 -
2e
Liebermann M.Tabet M.Sasaki T. J. Am. Chem. Soc. 1994, 116: 5035 -
2f
Palmer CR.Sloan LS.Adrian JCJ.Cuenoud B.Paolella DN.Schepartz A. J. Am. Chem. Soc. 1995, 117: 8899 - 3
Albrecht M.Napp M.Schneider M. Synthesis 2001, 468 -
4a
Albrecht M.Napp M.Schneider M.Weis P.Fröhlich R. Chem. Commun. 2001, 409 -
4b
Albrecht M.Napp M.Schneider M.Weis P.Fröhlich R. Chem.-Eur. J. 2001, 3966 - 5
Bodanszky M.Bodanszky A. The Practice of Peptide Synthesis Springer Verlag; Berlin: 1984. - 6
König W.Geiger R. Chem. Ber. 1970, 103: 788 -
7a
Bergeron RJ.Kline SJ.Stolowich NJ.McGovern KA.Burton PS. J. Org. Chem. 1981, 46: 4524 -
7b
Anderson GW.Zimmermann JE.Callahan FM. J. Am. Chem. Soc. 1964, 86: 1839 - 8
Albrecht M. Synthesis 1996, 230 - 9
Scarrow RC.White DL.Raymond KN. J. Am. Chem. Soc. 1985, 107: 6540 -
10a
Duhme A.-K.Dauter Z.Hider RC.Pohl S. Inorg. Chem. 1996, 35: 3059 -
10b
Duhme A.-K. J. Chem. Soc., Dalton Trans. 1997, 773 - 11
Kelso MJ.Hoang HN.Appleton TG.Fairlie DP. J. Am. Chem. Soc. 2000, 122: 10488