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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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An improved synthesis212 of (À) CIP-AS (54), an analogue of glutamic acid has been reported, which involves cycloaddition of ethoxycarbonyl formonitrile oxide to a N-(4-methoxybenzyl)a-ethoxycarbonyl nitrone. Further clarification213 has been given of the conditions that favour cyclopropane vis a` vis cyclopentene ring formation from a Schiff base derivative of glycine and bis-alkylating alkenes. Amino Acids, Pept. Proteins, 2006, 35, 1–73 19 The synthesis214 of 2-cyclopentadienylglycine (55) from a-bromohippuric acid with nickelocene, or other cyclopentadienyl complexes has provided a means of studying its dimerisation in Diels-Alder reactions and in ferrocenylene formation.

Another total synthesis125 of the selective glutamate receptor agonist dysiherbaine (22) has been reported, this time in a one-pot halogenation-ring-contraction to prepare the bicyclic ring system with excellent stereochemical control at the C-4 centre. N-Methylhydroxyleucine and another three unusual components (23– 25) of cyclomarin A have been synthesised126 in protected form ready for further processing to the cyclic peptide. Amino acid (23) was derived from diastereoselective methylation of an aspartic acid lactone, while (24) was formed via aldol reaction with Schollkopf’s chiral glycine enolate, and (25) was achieved by the AQN ligand-promoted Sharpless aminohydroxylation protocol.

Proteins, 2006, 35, 1–73 27 Although not strictly side–chain unsaturation, it is appropriate to record the preparation of N-allyl amino esters333 by either reaction of allylamine with Cl(CH2)nCOOEt or with ethyl acrylate, and the addition of a range of (hetero)aryl bromides to the alkyne function in N-propargyl alanine334 using a crosscoupling reaction catalysed by 10% Pd/C. 10 Synthesis of a-Amino Acids with Aromatic or Heterocyclic Side-Chains. – There has been a flurry of activity in incorporating fluorine into aromatic sidechains, for use as tracers in medical imaging (PET).

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