Solid-Phase Synthesis of a Double 4-Pyridinyl Terminated Leu-Ala-Leu Tripeptide and Macrocyclization by Palladium(II) Coordination

Markus Albrecht; Patrick Stortz; Marianne Engeser; Christoph A. Schalley

doi:10.1055/s-2004-835624

LETTER

Solid-Phase Synthesis of a Double 4-Pyridinyl Terminated Leu-Ala-Leu Tripeptide and Macrocyclization by Palladium(II) Coordination

Markus Albrecht*^a, Patrick Stortz^a, Marianne Engeser^b, Christoph A. Schalley^b
^a Institut für Organische Chemie der RWTH-Aachen, Professor-Pirlet-Strasse 1, 52074 Aachen, Germany
^b Kekulé-Institut für Organische Chemie und Biochemie, Universität Bonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany
Fax: +49(241)8092385; e-Mail: markus.albrecht@oc.rwth-aachen.de;

Abstract

Alle Artikel dieser Rubrik

Abstract

A Leu-Ala-Leu tripeptide, which bears pyridinyl units at the N- as well as C-terminus, is prepared by combination of solid- and solution-phase synthesis. With the Pd(en)²⁺ fragment it forms a mixture of 1:1 and 2:2 complexes, with the mononuclear complex probably being the dominating species.

Key words

solid-phase - coupling - pyridines - peptides - macrocycles

Volltext

Referenzen

References

1 Fersht A. Structure and Mechanism in Protein Science W. H. Freeman; New York: 1998.

2a Berg JM. J. Biol. Chem. 1990, 265: 6513

2b Weiss MA. Mason KA. Dahl CE. Keutmann HT. Biochemistry 1990, 29: 5660

3 Voyer N. In Topics in Current Chemistry Vol. 184: Schmidtchen FP. Springer Verlag; Berlin: 1997. p.1

4a Kelso MJ. Hoang HN. Appleton TG. Fairlie DP. J. Am. Chem. Soc. 2000, 122: 10488

4b Kelso MJ. Beyer RL. Hoang HN. Lakdawala AS. Snyder JP. Oliver WV. Robertson TA. Appleton TG. Fairlie DP. J. Am. Chem. Soc. 2004, 126: 4828

4c Snyder JP. Lakdawala AS. Kelso MJ. J. Am. Chem. Soc. 2003, 125: 632

5a Albrecht M. Stortz P. Weis P. Supramol. Chem. 2003, 15: 477

5b Albrecht M. Stortz P. Weis P. Synlett 2003, 867

5c Albrecht M. Stortz P. Runsink J. Weis P. Chem.-Eur. J. 2004, 10: 3657

6 Fujita M. Chem. Soc. Rev. 1998, 27: 417

7a Qin Z. Jennings MC. Puddephatt RJ. Inorg. Chem. 2003, 42: 1956

7b Qin Z. Jennings MC. Puddephatt RJ. Chem. Commun. 2002, 354

8a Millington CR. Quarrell R. Lowe G. Tetrahedron Lett. 1998, 42: 7201

8b Rosenbaum C. Waldmann H. Tetrahedron Lett. 2001, 42: 3677

9 Barlos K. Gatos D. Kallitsis J. Papaphotiu G. Sotiriu P. Wenging Y. Schäfer W. Tetrahedron Lett. 1989, 30: 3943

10a Li P. Xu J.-C. Chin. J. Chem. 2000, 18: 456

10b Li P. Xu J.-C. Tetrahedron 2000, 56: 9949

10c Speicher A. Klaus T. Eicher T. J. Prakt. Chem. 1998, 340: 581

11 Jones J. Synthese von Aminosäuren und Peptiden VCH; Weinheim: 1995.

12 Albrecht M. Spieß O. Schneider M. Weis P. Chem. Commun. 2002, 786

13 Schalley AC. Mass Spectrom. Rev. 2001, 20: 253

14 See, for example: Constable EC. Housecroft CE. Mundwiller S. J. Chem. Soc., Dalton Trans. 2003, 2112