By John S. Davies
Crucial reference resource for researchers within the pharmaceutical and allied industries, and on the biology/chemistry interface in academia. summary: crucial reference resource for researchers within the pharmaceutical and allied industries, and on the biology/chemistry interface in academia. learn more...
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Additional info for Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 36)
159 A catalytic asymmetric procedure for the preparation of b-amino acids (speciﬁcally b-substituted Asp derivatives) is reported. The Cinchona alkaloid catalyst benzoylquinine (BQ) mediates up to ﬁve distinct steps of a reaction pathway, 48 | Amino Acids, Pept. Proteins, 2007, 36, 19–81 This journal is c The Royal Society of Chemistry 2007 all in one reaction vessel. 160 Five- and six-membered cyclic b-amino acids have been prepared in a short and stereoselective manner. 161 Four novel b-amino acids bearing the canonical nucleobases guanine, cytosine, adenine, and thymine in the side chain, are synthesized starting from BOC-L-Asp-4-benzyl ester.
162 Enantiopure b-amino-g-hydroxy acids and g-amino-d-hydroxy acids have been prepared by stereodivergent synthesis from L-Asp and L-Glu, respectively. 163 While quite a number of synthetic approaches towards enantiopure a- and b3-amino acids are known, facile synthesis routes to the 2-branched b-amino acids are rare and limited to single compounds. Phosphoramidite-derived copper(I) catalysts readily facilitate the enantioselective 1,4-addition of dialkyl zinc reagents to nitro acrylates. 164 This process is a promising approach towards enantiomerically pure 2-branched b-amino acids.
The inclusion of a,a-disubstituted a-amino acids in a peptide may aﬀect its secondary or tertiary structure. a,a-Dimethylglycine (Aib) is the most available and studied member of this type of sterically constrained amino acids. Amino acids other than Aib are not readily available, and, therefore, their biological properties and applications, as sterically constrained scaﬀolds, are still awaiting systematic studies. 76 This study has also shown some limitation of the method, as it cannot be extended to a- or b-branched alkyl halides or Michael acceptors to be used for the dialkylation reaction.
Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 36) by John S. Davies