Increased stability of peptidesulfonamide peptidomimetics towards protease catalyzed degradation

Bioorganic and Medicinal Chemistry

Volumn 7, Issue 6, 1999, Pages 1043-1047

  De Bont, Dries B A ^a   Sliedregt Bol, Karen M ^a   Hofmeyer, Lovina J F ^a   Liskamp, Rob M J ^a  

^a UTRECHT UNIVERSITY   (Netherlands)

Author keywords

Aminoacids and derivatives; Isosteres; Peptides and polypeptides; Solid phase synthesis

Indexed keywords

AMINO ACID; PEPTIDE; SULFONAMIDE;

ARTICLE; CONTROLLED STUDY; DRUG DEVELOPMENT; DRUG STABILITY; ENZYME DEGRADATION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROLYSIS; MASS SPECTROMETRY; NONHUMAN; PROTEINASE INHIBITION; STEREOISOMERISM;

BINDING SITES; CATALYSIS; ENDOPEPTIDASES; PEPTIDES; SUBSTRATE SPECIFICITY; SULFONAMIDES;

EID: 0033018532     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(99)00021-8     Document Type: Article

References (19)

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13. We have introduced the term 'peptidosulfonamide' (Moree, W. J.; van der Marel, G. A.; Liskamp, R. M. J. J. Org. Chem. 1995, 60, 5157) for peptides containing β-amino sulfonamide residues. α-amino sulfonamides are not stable and therefore peptides containing these residues are not stable, see e.g.: Moree, W. J.; Van Gent, L. C.; Van der Marel, G. A.; Liskamp, R. M. J. Tetrahedron 1993, 49, 1133; Merricks, D.; Sammes, P. G.; Walker, E. R. H.; Henrick, K.; McPartlin, M. M.; J. Chem. Soc. Perkin Trans. 1 1991, 2170.
14. We have introduced the term 'peptidosulfonamide' (Moree, W. J.; van der Marel, G. A.; Liskamp, R. M. J. J. Org. Chem. 1995, 60, 5157) for peptides containing β-amino sulfonamide residues. α-amino sulfonamides are not stable and therefore peptides containing these residues are not stable, see e.g.: Moree, W. J.; Van Gent, L. C.; Van der Marel, G. A.; Liskamp, R. M. J. Tetrahedron 1993, 49, 1133; Merricks, D.; Sammes, P. G.; Walker, E. R. H.; Henrick, K.; McPartlin, M. M.; J. Chem. Soc. Perkin Trans. 1 1991, 2170.
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