The synthesis and properties of Gla- and Phe-containing analogues of cyclic RGD pentapeptidesAbbreviations: Generally, the three-letter amino acid nomenclature is used, except in Table 1 where single-letter nomenclature, Râ =â Arg, Gâ =â Gly, Dâ =â Asp, Fâ =â Phe, Sâ =â Ser, Kâ =â Lys, is used. Lower case in single-letter nomenclature implies D-configuration. EDCâ =â 1-ethyl-3-[3-(dimethylamino)propyl]carbodiimide·HCl, HATUâ =â O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate, TBTU =â 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate, HOBtâ =â N-hydroxybenzotriazole, Mtrâ =â 2,3,6-trimethyl-4-methoxyphenylsulfonyl.
Davies, John S.; Enjalbal, Christine; Nguyen, Corrine; Al-Jamri, Loai; Naumer, Christian; Davies John S.; Department of Chemistry, University of Wales, Swansea; Enjalbal Christine; Department of Chemistry, University of Wales, Swansea; Nguyen Corrine; Department of Chemistry, University of Wales, Swansea; Al-Jamri Loai; Department of Chemistry, University of Wales, Swansea; Naumer Christian; Department of Chemistry, University of Wales, Swansea
Журнал:
Journal of the Chemical Society, Perkin Transactions 1
Дата:
2000
Аннотация:
Cyclopentapeptides containing the Arg-Gly-Asp motif have been synthesised using solid-phase assembly of side-chain-protected linear precursors, followed by solution-phase cyclisation. The replacement of the Asp residue by γ-carboxyglutamic acid (Gla) is a novel feature which gives rise to an analogue which inhibits cell adhesion, yet its congeners do not show activity in binding assays with recombinant integrin receptors. NMR techniques support a β/γ-turn conformation in most of the analogues.
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