Amino Acids, Peptides and Proteins: An Introduction by H.D. Jakubke, J. Jeschkeit

By H.D. Jakubke, J. Jeschkeit

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Extra info for Amino Acids, Peptides and Proteins: An Introduction

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These include the aminolysis of halogenated carboxylic acids, the STRECKER synthesis, the azlactone and the hydantoin syntheses and the malonic ester synthesis. Later sections describe methods which can be used for the synthesis of isotopically labelled amino acids and some of the reactions which have been proposed to account for amino acid formation in the course of the development of life on the earth. Processes such as the catalytic hydrogenation of

An important preparative application of Sephadex types G 10 and G25 is the desalting of solutions of amino acids, peptides and proteins, which, until recently, could only be achieved by dialysis. 1. Paper Chromatography 50 This technique was first described in 1944 by CoNSDEN, GoRDON and MARTIN, and, in its two-dimensional version, is now widely used for the qualitative analysis of amino acids. Besides the original solvents phenoljwater (8: 2) and collidinejlutidine (1: 1, saturated with water) numerous other combinations have been found suitable for the resolution of the constituents of protein hydrolysates.

In a subsequent improvement the partial saponification was avoided by using cyanoacetic ester instead of malonic ester: / R-CH C==N "co oR C==N N2H4 ---+ CURTIUS rearrangement - - - - - - - - - - - + DL-amino acid nitrile hydrolysis 4* I R-CH I 36 Amino Acids E. FiscHER used the general malonic ester synthesis to obtain halogenated fatty acids which could then be converted into amino acids by ammonolysis. A valuable simplification of the malonic ester synthesis involves the use of N-protected aminomalonic acid derivatives, in an approach which avoids the lengthy procedure for the introduction of the amino group (SoRENSEN, 1903): the sodium salt of phthalimidomalonic ester is treated with an alkylhalide to give the corresponding DL-amino acid (usually in 60-80 per cent yield) after hydrolysis and decarboxylation: Oc co ~NK co COOR' I CHBr + c~ I -KBr COOR' COOR' 1 CsHsCH2Cl I C2HsONa ,N-CH co COOR' CO COOR' ' N-C-CH2-CsHs I I CO I COOR' DL-phenylalanlne Nowadays N-formylamino and N-acetylamino malonic esters are more important starting materials.

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