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By John S. Davies

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Extra resources for Amino Acids, Peptides and Proteins (SPR Amino Acids, Peptides, and Proteins (RSC)) (Vol 35)

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In an enzyme-assisted100 preparation of D-tert-leucine, it was (Æ)-N-acetyl-tert-leucine chloroethyl ester that exhibited the highest rate of hydrolysis. Amino acid anhydride hydrochlorides have been used101 for the first time as acylating agents in Friedel-Crafts reactions, resulting in the synthesis of Lhomophenylalanine from aspartic acid. Reduction of cystine with Fe/HCl yielded102 cysteine, while di- and tri-nuclear Cu(II) complexes catalysed103 the condensation of glycine with HCHO to yield serine.

HO H Me3N+ COOH O O H CO2H - OH OOC 4 O NH2 (20) (21) NH2Me H 3N + COO- (22) 12 Amino Acids, Pept. Proteins, 2006, 35, 1–73 The side-chain component of paclitaxel (taxol), (2R, 3S)-N-benzoyl-3-phenylisoserine, has been synthesised122 utilising dihydroxylation and regio-and diastereo-selective iminocarbonate rearrangement. N, N-Dichlorinated derivatives of taurine, homotaurine, GABA and leucine have been shown123 to be more lipophilic than their parent compounds, and an asymmetric synthesis124 of cis-a,b-propanoleucine has used a Strecker synthesis as a key step.

Fluorinated DL-phenylalanines were synthesised337 from fluorinated aromatic aldehydes by a ‘one-pot’ procedure involving Erlenmeyer reactions and subsequent reduction (P/HI). 338 The Erlenmeyer azlactone strategy has also been employed339 for the synthesis of 6-fluoro-meta-tyrosine from 2-fluoro-5-hydroxybenzaldehyde, and O-(2-[18F]-fluoroethyl)-L-tyrosine was made340 in a remote-controlled ‘no carrier added’ synthesis. 2-Fluoro- and 6-fluoro-(2S, 3R)-(3, 4-dihydroxy-phenyl)serines, were also produced341 via oxazolidine intermediates formed from 3, 4- (and 4, 5)dibenzyloxy-2-fluorobenzaldehyde respectively.

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