ACID STABILITY OF SEVERAL BENZYLIC PROTECTING GROUPS USED IN SOLID-PHASE PEPTIDE SYNTHESIS - REARRANGEMENT OF 0-BENZYLTYROSINE TO 3-BENZYLTYROSINE
ACID STABILITY OF SEVERAL BENZYLIC PROTECTING GROUPS USED IN SOLID-PHASE PEPTIDE SYNTHESIS - REARRANGEMENT OF 0-BENZYLTYROSINE TO 3-BENZYLTYROSINE
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DOI：
10.1021/ja00792a046
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发表时间：
1973-01-01
影响因子：
15
通讯作者：
MERRIFIELD, RB
中科院分区：
文献类型：
--
作者：
ERICKSON, BW;MERRIFIELD, RB
The acid stabilities of ten amino acid derivatives bearing benzylic side-chain protecting groups were determined quantitatively by ion-exchange chromatography. The apparent first-order rate constants for loss of the benzylic groups were measured in 50: 50 (v/v) trifluoroacetic acid-dichloromethane at 20. The derivatives and their rate constants (k, 10-8 sec-1) follow in order of increasing stability: O-benzyl-L-tyrosine (636)< V'-benzyloxycarbonyl-L-lysine (396)«O-benzyloxycarbonyl-L-tyrosine (89)~ S-(4-methoxybenzyl)-L-cysteine (82)«O-benzyl-L-serine (10.7)~ L-aspartic acid/3-benzyl ester (9)~
