Use of Onium Salt-Based Coupling Reagents in Peptide Synthesis1
Peptide coupling methods derived from onium salts based on 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) are becoming incorporated in synthetic strategies more frequently than the classical carbodiimide methods. We have correlated the reactivity of various onium salts derived...
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Published in | Journal of organic chemistry Vol. 63; no. 26; pp. 9678 - 9683 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
American Chemical Society
25.12.1998
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Online Access | Get full text |
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Summary: | Peptide coupling methods derived from onium salts based on 1-hydroxybenzotriazole (HOBt) and 1-hydroxy-7-azabenzotriazole (HOAt) are becoming incorporated in synthetic strategies more frequently than the classical carbodiimide methods. We have correlated the reactivity of various onium salts derived from HOXt (X = A, B), with the structure of the reagents in question. Thus, we confirmed that the aza derivatives are more reactive than the parent benzotriazole derivatives in both activation and coupling. In addition, the activation step is determined by the structure of the carbon skeleton. Thus, pyrrolidino derivatives appear to be reagents of choice relative to the piperidino analogues or those derived from trialkylamines. Furthermore although phosphonium salts are slightly less reactive than the corresponding aminium/uronium salts, the former should be used for the activation of hindered species, since the latter may lead to the formation of guanidino derivatives. |
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Bibliography: | istex:52B0B55562066E1B94FF11C418EDD8389EFC713F ark:/67375/TPS-C4HBVHTV-S |
ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/jo980807y |