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Extra info for Amino Acids and Peptides (SPR Amino Acids, Peptides (RSC))vol.21
A q . HCI Scheme 2 2 Amino Acids PhCONH Scheme 23 Reagents : i , R ~ C H = C H C R ~ R ~ O ; H ii, spontaneous hctero-Cope iii, boiling conc. HCL Scheme 2 4 rearrc'ingement; Amino Acids and Peptides 24 operated on a moderately large scale (45 g L-methionine gave 10 g of its a-methyl homologue). 13* 4 3 O t h e r A l Q b U ~ a p d ~ B e t e r o c v c l i c ~ h c i d s . -This section collects syntheses of aliphatic amino acids that, it so happens, are not known in natural sources. However, most of the methods are complementary to, or identical with, those in the preceding Sections of this Chapter.
Y-Amino acids are represented by simple examples ( 46 SO') and (R)-carnitine (Scheme 36)206 as far as stereospecif ic synthesis is concerned, but pre-eminently by the B-hydroxy-Y-amino acid, statine and its analogues, for which several new s y n t h e s e ~ ~ ~have ~ - ~ lbeen ~ reported. 20a Addition of the chiral acetate enolate CH2=C(OLi)CHPhCPh20Li,z0sand of anions of malonate half-estersIm0 to a-(Boc-amino)aldehydes, and condensation of malonic esters with E-protected amino acids2) 'l2 followed by reduction (including yeast-catalyzed reduction2"), provide alternative routes to statines.
Acids in preceding Volumes of this Report are featured again this year, with everincreasing medical interest in short-lived "C and IBF isotopomers. Coverage in this Section is in order of ascending atomic mass. 225 C 3-l )C1-DL-Alanine, a-aminoisobutyric acid, norvaline, norleucine and phenylalanine have been synthesized by phase-transfer alkylation of E(diphenylmethy1ene)glycine tert-butyl ester, and L-enantiomers of alanine and ether method. 227 L- and D-Cl-methionines can be (and correspondingly labelled prepared by methylation of S-benzylhomo~ysteines~~~ selenomethionine~~~~), and from L-homocysteine thiolactone.