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Synthesis 2002(14): 2091-2095
DOI: 10.1055/s-2002-34378
DOI: 10.1055/s-2002-34378
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis and Conformational Analysis of a Novel Ansadipeptide
Further Information
Received
13 June 2002
Publication Date:
26 September 2002 (online)
Publication History
Publication Date:
26 September 2002 (online)
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
-
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