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Extra resources for Amino Acids and Peptides (SPR Amino Acids, Peptides (RSC))vol. 24
16I The presence of baker's yeast achieves up to 60% enantiomeric excesses, enhanced further by the presence of c y c l o d e ~ t r i n . '~' Efficient and practical syntheses of (R)-3-aminobutanoic acid starting from Lasparagine have been developed,'" through elaboration of the derived N,N-dibenzyl-L-asparaginol methanesulphonate via the nitrile. ) by Curtius rearrangement of 3-deuteriated malic acid (50; R 2 = C 0 2 H ) . itself prepared through enzymecatalyzed methods. 265 An enolate Claisen rearrangement of a 6-amino acid ally1 ester shown in Scheme 24 has been used for P-proline s y n t h e ~ i s .
12 Syntlzesis of N-Substituted a-Amino Acids While this Section excludes peptides, it includes non-routine examples of side-chain N-acyl- and N-alkyl derivatives. 13 Sjnthesis of a-Amino Acids Carrying Phosphorus-Containing Side-Chains Organic synthesis is responding more noticeably to the biological importance of glycosylated, phosphated and sulphated side-chains. The enhanced response is also stimulated for other reasons, and has been significantly helped by simplified synthesis methodology. 238(2R,3S)-P-(Phosphonoxyacetyl)pipecolic acid has been synthesised from N-(3-chloropropy1)-D-aspartic acid for the same p ~ r p o s e .
A standard technique, exemplified in resolution of chiral p-amino acids,3" uses N-dodecyl-hydroxy-L-proline bonded to C- 18 silica with a copper(I1) acetate buffer, but there are numerous variations of this protocol. Thus, copper(I1) acetate and 5'-guanosine monophosphate or cyanocobalamin have been shown to effect resolution of DL-3Hlabelled a-amino acids,328and copper(I1) salts of ribonucleic acids have been used as components of the mobile p h a ~ e . ~ ~ V last-mentioned his study was stimulated by the possible role of homochiral polynucleotides in bringing about the dominance of L-amino acids from prebiotic times, an aspect of resolution featured in the next Section of this Chapter.
Amino Acids and Peptides (SPR Amino Acids, Peptides (RSC))vol. 24 by J. S. Davies
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