BOP

Peptide coupling reagent which suppresses enantiomerization ^{[1,2,3,4,5,6,7,8,9,10,11,12,13,14,15]}. Reduction of carboxylic acids activated with BOP provides a facile route to alcohols ^[16]. Novabiochem^® recommends the replacement of BOP by PyBOP (for PyBOP please see 851009). The manufacture of BOP, as well as its utilization, involves the use or the formation of hexamethylphosphotriamide, the carcinogenicity and respiratory toxicity of which has been the subject of numerous reports.

Associated Protocols and Technical Articles

Guide to Selection of Coupling Reagents Literature references

^[1] B. Castro, et al. (1975) Tetrahedron Lett., 16, 1219.
^[2] B. Castro, et al. (1976) Synthesis, 751.
^[3] B. Castro, et al. (1977) Synthesis, 413.
^[4] B. Castro, et al. (1977) J. Chem. Res. (S), 182.
^[5] P. Rivaille, et al. (1980) Tetrahedron, 36, 3413.
^[6] D. L. Nguyen, et al. (1985) J. Chem. Soc., Perkin Trans. 1, 1025.
^[7] D. L. Nguyen, et al. (1987) J. Chem. Soc., Perkin Trans. 1, 1915.
^[8] A. Fournier, et al. (1988) Int. J. Peptide Protein Res., 31, 86 and 231.
^[9] J.-P. Briand, et al. (1989) Pept. Res., 2, 381.
^[10] A. Fournier, et al. (1989) Int. J. Peptide Protein Res., 33, 133.
^[11] D. L. Nguyen, et al. (1989) Biochem. Biophys. Res. Commun., 162, 1425.
^[12] W. K. Rule, et al. in ′Peptides 1988, Proc. 20th European Peptide Symposium′, G. Jung & E. Bayer (Eds), Walter de Gruyter, Berlin, 1989, pp. 238.
^[13] M. Forest, et al. (1990) Int. J. Peptide Protein Res., 35, 89.
^[14] R. Seyer, et al. (1990) Int. J. Peptide Protein Res., 35, 465.
^[15] H. Gausepohl, et al. in ′Innovation & Perspectives in Solid Phase Synthesis, 2nd International Symposium′, R. Epton (Eds), Intercept UK Ltd., Andover, 1993, pp. 387.
^[16] R. P. McGeary (1998) Tetrahedron Lett., 39, 3319.

Replaces: 01-62-0001

Color (visual): white to slight yellow to beige
Appearance of substance (visual): powder
Identity (IR): passes test
Assay (HPLC, area%): ≥ 99.0 % (a/a)
Solubility (0.6 mmole in 1 ml DMF): clearly soluble

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