Summary
X-ray diffraction structure determinations of HOAt and HOOBt, two well-known additives for peptide bond formation, are reported in conjunction with those of seven derivatives of HOBt, HOAt, and HOOBt, five of which originate from Nα-protected α-amino acids. In the crystal state the two additives are found in the 1-hydroxy tautomeric form. In contrast to six derivatives which crystallize as esters, one, Fmoc-(N)OBt, is observed in the isomeric amide-type (urethane) form.
Similar content being viewed by others
References
Toniolo, C., Crisma, M. and Formaggio, F., Biopolymers (Pept. Sci.), 40 (1996) 627.
König, W. and Geiger, R., Chem. Ber., 103 (1970) 788.
Knorr, R., Trzeciak, A., Bannwarth W. and Gillessen, D., Tetrahedron Lett., (1989) 1927.
Carpino, L.A., J. Am. Chem. Soc., 115 (1993) 4397.
Carpino, L.A., El-Faham, A., Minor, C. and Albericio, F., J. Chem. Soc., Chem. Commun., (1994) 201.
König, W. and Geiger, R., Chem. Ber., 103 (1970) 2024.
König, W. and Geiger, R., Chem. Ber., 103 (1970) 2034.
Atherton, E., Cameron, L., Meldal, M. and Sheppard, R., J. Chem. Soc., Chem. Commun., (1986) 1763.
Akaji, K., Kuriyama, N. and Kiso, Y., Tetrahedron Lett, 35 (1994) 3315.
Bosch, R., Jung, G. and Winter, W., Acta Crystallogr., C 39 (1983) 1089.
Pfister-Guillouzo, G., Gracian, F., Paez, J.A., Garcia-Gomez, C. and Elguero, J., Spectrochim. Acta, A51 (1995) 1801.
Vlassi, M., Germain, M., Barlos, K., Mamos, P. and Refaat, L.S., Z. Kristallogr., 192 (1990) 59.
McCarthy, D.G., Hegarty, A.F. and Hathaway, B.J., J. Chem. Soc., Perkin Trans. 2 (1977) 224.
Barlos, K., Papaioannu, D., Voliotis, S., Prewo, R. and Bieri, J.H., J. Org. Chem., 50 (1985) 696.
Sliedregt, K.M., Schouten, A., Kroon, J. and Liskamp, R.M.J., Tetrahedron Lett., 37 (1996) 4237.
Singh, J., Fox, R., Wong, M., Kissick, T.P., Moniot, J.L., Gougoutas, J.Z., Malley, M.F. and Kocy, O., J. Org. Chem., 53 (1988) 205.
Nagarajan, S., Wilson, S.R. and Rinehart Jr., K.J., J. Org. Chem., 50 (1985) 2174.
Abdelmoty, I., Albericio, F., Carpino, L.A., Foxman, B.M. and Kates, S.A., Lett. Pept. Sci., 1 (1994) 57.
Henklein, P., Costisella, B., Wray, V., Domke, T., Carpino, L.A., El-Faham, A., Kates, S.A., Abdelmoty, I. and Foxman, B.M., In Ramage, R. and Epton, R. (Eds.) Peptides 1996, Mayflower Worldwide, Kingswinford, U.K., 1998, in press.
Leplawy, M.T., Jones, D.S., Kenner, G.W. and Sheppard, R.C., Tetrahedron, 11 (1960) 39.
Crisma, M., Moretto, V., Valle, G., Formaggio, F. and Toniolo, C., Int. J. Pept. Protein Res., 42 (1993) 378.
Paquet, A., Can. J. Chem., 60 (1982) 976.
Sheldrick, G.M., SHELXS 86, Program for the Solution of Crystal Structures, University of Göttingen, Göttingen, Germany, 1986.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. and Camalli, M., J. Appl. Crystallogr., 27 (1994) 435.
Sheldrick, G.M., SHELX 76, Program for Crystal Structure Determination, University of Cambridge, Cambridge, U.K., 1976.
Allen, F.A., Kennard, O., Watson, D.G., Brammer, L., Orpen, A.G. and Taylor, R., J. Chem. Soc., Perkin Trans. 2, (1987) S1.
Ramakrishnan, C. and Prasad, N., Int. J. Protein Res., 3 (1971) 209.
Taylor, R., Kennard, O. and Versichel, W., Acta Crystallogr., B40 (1984) 280.
Görbitz, C.M., Acta Crystallogr., B45 (1989) 390.
Brown, I.D., Acta Crystallogr., A32 (1976) 24.
Mitra, J. and Ramakrishnan, C., Int. J. Pept. Protein Res., 9 (1977) 27.
Toniolo, C. and Benedetti, E., Macromolecules, 24 (1991) 4004.
Toniolo, C., Crisma, M., Formaggio, F., Valle, G., Cavicchioni, G., Précigoux, G., Aubry, A. and Kamphuis, J., Biopolymers, 33 (1993) 1061.
Nyburg, S.C. (Ed.) X-Ray Analysis of Organic Structures, Academic Press, New York, NY, 1961.
Llamas Saiz, A.L. and Foces-Foces, C., J. Mol. Struct., 238 (1990) 367.
Carpino, L.A., El-Faham, A. and Albericio, F., J. Org. Chem., 60 (1995) 3561.
Johnson, C.K., ORTEP II. Report ORNL-5138, Oak Ridge National Laboratory, Tennessee, 1976.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Crisma, M., Valle, G., Moretto, V. et al. Reactive intermediates in peptide synthesis: Molecular and crystal structures of HOAt and HOOBt, and some ester and amide derivatives of HOBt, HOAt and HOOBt. Lett Pept Sci 5, 247–258 (1998). https://doi.org/10.1007/BF02443541
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF02443541