476167-89-2Relevant academic research and scientific papers
Palladium(0)-catalyzed regioselective synthesis of α-dehydro-β-amino esters from amines and allyl acetates: Synthesis of a α-dehydro-β-amino acid derived cyclic peptide as a constrained β-turn mimic
Rajesh,Banerji, Biswadip,Iqbal, Javed
, p. 7852 - 7857 (2007/10/03)
Acetates derived from the adducts of the Baylis-Hillman reaction can be reacted in a regioselective manner with amines in the presence of palladium(0) catalyst to afford α-dehydro-β-amino esters (2 and 3) in good yields. The regioselectivity of the reaction can be controlled by temperature and reaction medium leading to the synthesis of regioisomers 2 or 3. The α-dehydro-β-amino acid 3 is a turn inducer, and the dipeptides 6 derived from it show the presence of an eight-membered intramolecular hydrogen bond. Also, cobalt(II) chloride catalyzes the cleavage of epoxy peptides with α-dehydro-β-amino acid derivative 3b to afford the corresponding dipeptide derivatives 8, which exhibit an intramolecular hydrogen bond and thus mimic a β-turn. This intramolecular hydrogen bonding preorganizes the corresponding diallylated peptide 8c for cyclization via ring-closing metathesis to afford the cyclic peptide 9 as a constrained mimic of a β-turn.
α-Dehydro β-amino acid derivatives as turn inducer: Synthesis of potential HIV protease inhibitors based on structural mimicry
Rajesh,Srivastava,Banerji,Iqbal
, p. 1029 - 1032 (2007/10/03)
α-Dehydro β-amino acid derivatives derived di- and tripeptides 4-7 adopt eight-member turn conformations in CDCl3 solutions. These peptides show similar hydrogen bonding characterstics as compared to the corresponding L-proline containing pepti
