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The 4 to 6 ratio for BocAspOH (g) was 11 due in part to the need for two O-alkylation reactions to produce the ester product (4) The additional enhancement in selectivity achieved with 3-mercaptopropanoic acid was likely due to coordination between the pendant thiol functionality and the intermediate diazonium ion, hindering external attack from water (J. R. Larson and N. D. Epiotis, J. Am. Chem. Soc., 1981, 103, 410-416)
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Notably, Glu111 (A. Tarragona-Fiol, H. J. Eggelte, S. Harbron, E. Sanchez, C. J. Taylorson, J. M. Ward and B. R. Rabin, Protein Eng., 1993) and Asp121 (L. W. Schultz, D. J. Quirk and R. T. Raines, Biochemistry, 1998, 37, 8886-8898)
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Notably, Glu111 (A. Tarragona-Fiol, H. J. Eggelte, S. Harbron, E. Sanchez, C. J. Taylorson, J. M. Ward and B. R. Rabin, Protein Eng., 1993, 6, 901-906) and Asp121 (L. W. Schultz, D. J. Quirk and R. T. Raines, Biochemistry, 1998, 37, 8886-8898) have been implicated in the catalytic activity of RNase A
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, vol.6
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