By P Karlson (Auth.)
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Extra info for Introduction to Modern Biochemistry
Its name points to the relationship with the sugar threose. Threonine has two asymmetric centers (cf. Chap t. 1-4) manifested by four stereoisomeric forms of which two are always mirror images of the other two; namely D- and L-threonine and D- and L-allothreonine. Threonine was discovered in an interesting manner: it was identified as a necessary supplementary factor of a synthetic diet mixture (Rose 1935) and thus became the first amino acid to be recognized as indispensable. CH3 H2C—OH I Θ H—C — NH3 c—oQ ^0 L-Serine H — C—OH Θ I H3N—C—H c^oe ^0 D-Threonine CH3 CH3 HO — C—H 1 ® H—C-NH3 c—oe ^0 L-Threonine I H — C — OH I ® H—C— NH3 e c-o L-Allothreonine Cysteine (α-amino-ß-mercaptopropionic acid) contains sulfur.
A ^0« 02/V—(/ \-NH—CH—C—Oe > \u \ 0 N02 R2 R2 ® ! <^°<=> H3N—CH—C — 0°+· NO2 Finally, enzymic methods are available for the cleavage of larger peptides and for the identification of terminal groups (cf. Chapt. VIII-3). Long sequences have been established in this way. Peptide Synthesis. Any synthesis of peptides must resort to some activation (cf. Chapt. 1-2) of the carboxyl or the amino group. One of the oldest methods of organic chemistry involves acid chlorides. g. by a carbobenzoxy residue: J (/ y 0 \-CH2-0-C-N H yC > COOH > (/ y 0 H yC H-N \—CH2-0-C-N C-Cl* COOH CH *2 R1 -ne /r\_ > K x=/ /ÀÂ/ y—CH2—o-c—N H 00 c CH 0 R2 ii r Rf " ^ > ÀÂ/00" H2N c ii 0 + P cH i R2 y—CH3+C02 The protective carbobenzoxy group may subsequently be removed by hydrogenolysis (cleavage by catalytically activated hydrogen).
Of biochemical significance is the formation of amides. Ammonia affords unsubstituted amides s° *° R—CH—C—NH2 R-CH-C-NH-R NH2 NH2 while amines produce substituted amides, better known as peptides (cf. Chapt. III). Salt formation, again, is also one of the reactions of the amino group. As with ammonia, it consists of an addition of a proton from another acid: /0 R-CH-C—OH + H®+ C / 0 0 R-CH-C-OH > NH2 + Cle ®NH3 Another important reaction is acylation, which yields again acid amides. The acetyl and benzoyl derivatives of glycine (the latter is called hippuric acid) occur naturally, in addition to a few other compounds of similar composition.