Amino Acids and Peptides (SPR Amino Acids, Peptides by J. H. Jones PDF
By J. H. Jones
Expert Periodical stories offer systematic and designated evaluation assurance of development within the significant components of chemical study. Written through specialists of their professional fields the sequence creates a special carrier for the energetic study chemist, delivering normal serious in-depth debts of development particularly parts of chemistry.
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Additional resources for Amino Acids and Peptides (SPR Amino Acids, Peptides (RSC))vol.21
2 Ws%&yJd analysis of amino acids, since the main principles of methodology are well established. One of these established principles is derivatization of amino acids in order to achieve adequate volatility, although pyrolysis-g. c. g. ~~' H-Trifluoroacetylamino acid n-butyl esters, isobutyl esters,44s and nb~tylamides~~" continue to have their champions; in one of these papers, the simple change of solvent from CHzClz to CHC13 for the acylatfon step is shown to be beneficial. c. S. p. c. and ion-exchange methods.
A high yield route (Scheme 34) is based on alkylation of amine oxides with vinyl ethers. l ye Hydrocyanation of phthal imido-alkynes catal yzed by nickel powder leads to mixtures of B- and Y-amino acids. l Y y Particular examples of synthesis targets include (8) -isoserine HHaCHaCH (OH)C02H, for which three independent studies claim the first enantioselective synthesis. (8)-Malic acid, ( 43 formed with (Ph0)2P(O)B3 and Et3B in refluxing benzene,200 or Curtius rearrangement of ( 44 1, 20' and (-1-8-phenylmenthyl glyoxylate m ~ n o h y d r a t e , are ~ ~ ~ the chosen starting materials.
12= The other B-hydroxylated a-amino acids covered this year present fearsome stereochemical challenges; these have been well confronted, syntheses of the hydroxy-amino acid moiety of AI-77-B, a gastroprotective AI-77 ( 25 ) being notable (Scheme 18). substance from Bacillus A general asymmetric synthesis for 8-hydroxy-a-Emethylamino acidsn7 involving efficient Sharpless epoxidation of an appropriately located side-chain double bond (but depending on the presence of a 1-CH2 group) has been developed as a result of the ongoing interest in routes to 'MeBmt', the non-protein a-amino acid (4B)-4[ (E)-2-butenyll-4-m-dimethyl-L-threonine of cyclosporin.
Amino Acids and Peptides (SPR Amino Acids, Peptides (RSC))vol.21 by J. H. Jones