Synthesis and Conformational Analysis of a Novel Ansadipeptide

Abstract

A novel ansapeptide 6 was synthesized from tyrosine (5) and Bic 3b as the amino acid components and oxalic acid as the connecting link. The conformational properties of 6 were calculated by molecular mechanics.

Key words

ansa compounds - peptidomimetics - β-amino acids - conformation analysis - molecular mechanics

References

• 1a Kase M. Kaneko M. Yamada K. J. Antibiot.  1987,  40:  450 
• 1b Yasuzawa T. Shirahata T. Sano H. J. Antibiot.  1987,  40:  455 
• 2 Xue C.-H. He X. Roderick J. DeGrado WF. Cherney RJ. Hardmann KD. Nelson J. Copeland RA. Jafee BD. Decicco CP. J. Med. Chem.  1998,  41:  1745 
• 3 Decicco CP. Song Y. Evans DA. Org. Lett.  2001,  3:  1029 
• 4a Cawston TE. Pharm. Ter.  1996,  70:  163 
• 4b Johnson LL. Dyer R. Hupe D. J. Curr. Opin. Chem. Biol.  1998,  2:  466 
• 4c Massova I. Kotra LP. Fridmann R. Mobashery S. FASEB J.  1998,  12:  1075 
• 5 Cispentacin = 2-aminocyclopentanecarboxylic acid (2-ACPC), for a related approach using trans-4-hydroxy-proline as a template see: Arasappan A. Chen KX. Njoroge FG. Parekh TN. Girijavallabhan V. J. Org. Chem.  2002,  67:  3923 
• 6 Petzold K. Dahl H. Skuballa W. Gottwald M. Liebigs Ann. Chem.  1990,  1087 
• 7 Kong Y. Ponder JW. J. Chem. Phys.  1997,  107:  481 
• See for example:
• 8a Hanessian S. McNaughton-Smith G. Lombart H.-G. Lubell WD. Tetrahedron  1997,  53:  12789; and references therein 
• 8b Mulzer J. Schülzchen F. Bats J.-W. Tetrahedron  2000,  56:  4289 
• See for example:
• 9a Baures PW. Ojala WH. Gleason WB. Johnson RL. J. Pept. Res.  1997,  50:  1 
• 9b Nagai U. Sato K. Nakamura R. Kato R. Tetrahedron  1993,  47:  3577 
• 9c Mueller R. Revesz L. Tetrahedron Lett.  1994,  35:  4091 
• 9d Hibbs DE. Hursthouse MB. Jones IG. Jones W. Abdul Malik KM. North M. J. Org. Chem.;  and references therein
• 9e Jones IG. Jones W. North M. J. Org. Chem.  1998,  63:  1505 ; and references therein
• 10 Kutscher B. Bernd M. Beckers T. Polymeropulos EE. Engel J. Angew. Chem., Int. Ed. Engl.  1997,  36:  2148 ; Angew. Chem. 1997, 109, 2240