By John A. Sturman, Derek A. Applegarth (auth.), Alan A. Boulton, Glen B. Baker, James D. Wood (eds.)
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Additional resources for Amino Acids
The derivatrzatlon sequence 1s illustrated in Fig. 4 for serme. Compared with estenfrcation procedures, the formation of cyclic derivatives, as lust described, has certain advantages: (a) GC of Amino HO Aads “f 39 cool-i ,CF,CI NH, + O=Y C F,CI -Ii,0 I HO%? 0 0 l-4 F% acetylation HFBA CF,CI Cl F,C 4 Derlvatlzatlon : C,F,CO 0 7-s H Y Cl F,C CF,CI of Ser by cycllzatlon followed by the cychzation reaction proceeds readily to completion at room temperature, and both the -COOH and the -NH2 groups of cy-ammo acids are modified in a single chemical reaction; (b) Gln and Asn are not hydrolyzed because of the mild reaction condltrons, and (c) the cyclic derivatives are sensitive to ECD.
1981). , 1984) The method involves the rsocarboxycarbonylatron of the amme, followed by conversion of the sulfomc acid moiety to sulfonyl chloride. The sulfonyl chlorrde is subsequently condensed with a secondary amine to form a sulfonamide (Fig 8) that is analyzed on an OV-17 column. This procedure appears to be sensmve and specific for Tau. SOCl2 -I-BuOCOCl H2NCH2CH2S03H e A-BuOCONHCH2CH2S03 NaOH -I-BuOCONHCH2CH2SO2Cl Fig. 8 Derwatlzatlon nation, and amldatlon. e A-BuOCONHCH2CH2S02NR2 of Tau by lsobutoxycarbonylatlon, chlon- 8.
1983). Pentafluorobenzoyl chloride (PFBC), therefore, was chosen to derrvatlze the other reactrve groups of the amino acid rsobutyl esters. Pentafluorobenzoylation (Fig. 7) was conducted at room temperature in aqueous condrtrons. -I-BuOH/ H+ R-COO-i - -Bu R-COOH PFBC R-NH2 R-m-cot 6F 5 NaHC03 R-OH R-SH Fig 7. Derlvatlzatlon of ammo acids by esterlficatlon pentafluorobenzoylatlon. followed by 42 Coutts and Yeung More than 20 ammo acids can be analyzed by this procedure m less than 20 min on a fused srlrca capillary column with ECD.