Abstract
Abstract: Enantiopure 6,7-diacetoxy-3- t -butoxycarbonylamino-azabicyclo[3.3.0]octan-2-one-8-carboxylic acid 14 (pyrrolizidi-none amino acid) was synthesized in 14 steps and 5.8% overallyield from tri- O -benzyl- D -arabinose 5 through the formyl C -imino-sugar 9 as a key intermediate. Key words: integrins, peptidomimetics, pyrrolizidinone aminoacids, reverse-turn, RGD The field of peptidomimetics 1 has gained an enormousimportance in recent years, particularly with the emer-gence of conformationally constrained systems that mim-ic certain structural features and therapeutic effects ofnatural peptides. 2 A special class of rigidified peptidomi-metics is constituted of the azabicyclo[X.Y.0]alkanoneamino acids 2b,3 1 (Figure 1), i. e. fused bicyclic dipeptidesthat simulate the bioactive conformation of the b-turnsites. 4 The stereocontrol 3,5 at the chiral carbon backboneand ring-fusion center, the side chain attachment, 6,7b andthe ring size, 5,8 are issues, which have been widely ad-dressed. These molecules have been used not only tomimic a dipeptide motif
Published Version
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