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

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

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