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Growth Factors Volume 20, 2002 - Issue 2
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Research Article

Rapid Microscale Enzymic Semisynthesis of Epidermal Growth Factor (EGF) Analogues

E.C. Nice Ludwig Institute for Cancer Research, Melbourne Tumour Biology Branch, P.O. Box 2008, Royal Melbourne Hospital, Melbourne, Victoria 3050, Australia
,
T. Domagala Ludwig Institute for Cancer Research, Melbourne Tumour Biology Branch, P.O. Box 2008, Royal Melbourne Hospital, Melbourne, Victoria 3050, Australia
,
L. Fabri Ludwig Institute for Cancer Research, Melbourne Tumour Biology Branch, P.O. Box 2008, Royal Melbourne Hospital, Melbourne, Victoria 3050, Australia
,
M. Nerrie Ludwig Institute for Cancer Research, Melbourne Tumour Biology Branch, P.O. Box 2008, Royal Melbourne Hospital, Melbourne, Victoria 3050, Australia
,
F. Walker Ludwig Institute for Cancer Research, Melbourne Tumour Biology Branch, P.O. Box 2008, Royal Melbourne Hospital, Melbourne, Victoria 3050, Australia
,
R.N. Jorissen Ludwig Institute for Cancer Research, Melbourne Tumour Biology Branch, P.O. Box 2008, Royal Melbourne Hospital, Melbourne, Victoria 3050, Australia
,
A.W. Burgess Ludwig Institute for Cancer Research, Melbourne Tumour Biology Branch, P.O. Box 2008, Royal Melbourne Hospital, Melbourne, Victoria 3050, Australia
,
D.-F. Cui Shanghai Institute of Biochemistry and Cell Biology, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Shanghai, 200031, People's Republic of China
&
Y.-S. Zhang Shanghai Institute of Biochemistry and Cell Biology, Shanghai Institute for Biological Sciences, Chinese Academy of Sciences, Shanghai, 200031, People's Republic of China
 show all
Pages 71-80 | Published online: 11 Jul 2009

  • Acharya, A.S., Khan, S.A. and Seetharam, R. (1985) "Semisynthesis of a-chain of hemoglobin S: V8-protease catalyzed conversion of the non-covalent fragment system to covalent form", In: Deber, C.M., Hruby, V.J. and Kopple, K.D., eds, Proceedings of the Ninth American Peptide Symposium (Pierce Chemical Company, Rockford, USA), pp 335-338.
  • Barnham, K.J., Torres, A.M., Alewood, P.P., Domagala, T., Nice, E.C. and Norton, R.S. (1998) "Role of the 6-20 disulfide bridge in the structure and activity of epidermal growth factor", Protein Sci. 7, 1738-1749.
  • Burgess, A.W. and Sizeland, A.M. (1990) "Growth factors and the gut", J. Gastroenterol Hepatol. 5(Suppl. 1), 10-21.
  • Burgess, A.W., Knesel, J., Sparrow, L.G., Nicola, N.A. and Nice, E.C. (1982) 'Two forms of murine epidermal growth factor: rapid separation by using reverse-phase HPLC'", Proc. Ncal. Acad. Sci USA 79, 5753-5757.
  • Burgess, A.W., Lloyd, C.J. and Nice, E.C. (1983) "Murine epidermal growth factor: heterogeneity on the high resolution ion-exchange chromatography", EMBO J. 2, 2065-2069.
  • Burgess, A.W., Lloyd, C.J., Smith, S., Stanley, E., Walker, P., Fabri, L., Simpson, R.J. and Nice, E.C. (1988) "Murine epidermal growth factor: structure and function", Biochemistry 27, 4977-4985.
  • Campbell, I.D., Cooke, R.M., Baron, M., Harver, T.S. and Tappin, M.J. (1989) 'The solution structures of epidermal growth factor and transforming factor alpha", Prog. Growth Factor Res. 1, 13-22.
  • Cao, Q.P., Cui, D-F. and Zhang, Y.S. (1981) "Enzymatic synthesis of deshexapeptide insulin", Nature 292, 774-775.
  • Carver, J.A., Cooke, R.M., Esposito, G., Campbell, D., Gregory, H. and Sheard, B. (1986) "A high resolution 1H NMR study of the solution structure of human epidermal growth factor", FEBS Lett. 205, 77-81.
  • Chang, W., Upton, C., Hu, S-L, Purchio, A.F. and McFadden, G. (1987) "The genome of the Shope fibroma virus, a tumourogenic poxvirus, contains a growth factor gene with sequence similarity to those encoding epidermal growth factor and transforming growth factor a", MoI. Cell Biol. 7, 535-540.
  • Cohen, S. (1962) "Isolation of a mouse submaxillary-gland protein accelerating inicisor eruption and eyelid opening in the new-born animal", J. Biol Chem. 237, 1555-1562.
  • Cohen, S. (1965) "The stimulation of epidermal proliferation by a specific protein (EGF)", Deu Biol 12, 394.
  • Cohen, S. and Elliot, G.A. (1963) "The stimulation of epidermal keratinization by a protein isolated from the submaxillary gland of the mouse", J. Investig. Dermatol. 40, 1-5.
  • Cooke, R.M., Wilkinson, A.J., Baron, M., Pastore, A., Tappin, M.I., Campbell, L.D., Gregory, H. and Sheard, B. (1987) "The solution structure of human epidermal growth factor", Nature 327, 339-341.
  • Defeo-Jones, D., Tai, J.Y., Wegrzyn, R.J., Vuocolo, G.A., Baker, A.E., Payne, LS., Garsky, V.M., Oliff, A. and Riemen, M.W. (1988) "Structure-function analysis of synthetic and recombinant derivatives of transforming growth factor alpha", MoI. Cell Biol. 8, 2999-3007.
  • Derynck, R., Roberts, A.B., Winkler, M.E., Chen, E.Y. and Goeddel, D.V. (1984) "Human transforming growth factor a: precursor structure and expression in E. coK", Cell 38, 287-297.
  • Engler, D.A., Matsunami, R.K., Campion, S.R., Stringer, C.D., Steens, A. and Niyogi, S.K. (1988) "Cloning of authentic human epidermal growth factor as a bacterial secretory protein and its initial structurefunction analysis by site-directed mutagenesis", J. Biol. Chem. 263, 12384-12390.
  • Fabri, L, Maruta, H., Muramatsu, H., Muramatsu, T., Simpson, R.I., Burgess, A.W. and Nice, E.C. (1993) "Structural characterization of native and recombinant forms of the neurotrophic cytokine MK", J Chromatogr. 646, 213-225.
  • Graf, L. and Li, C-H. (1981) "Human somatotrophin: covalent reconstitution of two polypeptide contiguous fragments with thrombin", Pmc. Natl Acad. Sci. USA 78, 6135-6138.
  • Grego, B., Nice, E.C. and Simpson, R.J. (1986) "Use of scanning diode array detector with reversed phase microbore columns for real time spectral analysis of aromatic amino acids in peptides and proteins at the submicrogram level", J. Chromatogr. 352, 359-368.
  • Gregory, H. (1975) "Isolation and structure of urogastrone and its relationship to epidermal growth factor", Nature 257, 325.
  • Gregory, H., Thomas, C.E., Young, I.A., Wiltshire, I.R. and Garner, A. (1988) "The contribution of the C-terminal undecapeptide sequence of urogastron-epidermal growth factor to its biological action", Regul. Pept. 22, 217-226.
  • Groenen, L.C., Nice, E.C. and Burgess, A.W. (1994) "Structure-function relationships for the EGF/TGF-alpha family of mitogens", Growth Factors 11, 235-257.
  • Higashiyama, S., Abraham, I.A., Miller, J., Fiddes, LC. and Klagsburn, M. (1991) "A heparin-binding growth factor secreted by macrophage like cells that is related to EGF', Science 251, 936-939.
  • Inouye, K., Watanbe, K., Morihara, K., Tochino, Y, Kanaya, T. and Emura, J. (1979) "Enzyme-assisted semi-synthesis of human insulin", J. Am. Chem. Soc. 101, 751-752.
  • Jones, J.T., Akita, R.W. and Sliwkowski, M.X. (1999) "Binding specificities and affinities of egf domains for ErbB receptors", FEBS Lett. 447, 227-231.
  • Kasche, V. (1989) "Proteases in peptide synthesis", In: Beynon, R.J. and Bond, J.S., eds, Proteolytic Enzymes--A Practical Approach (IRL Press, Oxford), pp 125-143.
  • Kimura, H., Fischer, W.H. and Schubert, D. (1990) "Structure, expression and function of a schwannoma-derived growth factor", Nature 348, 257-260.
  • Koide, H., Yokoyama, S., Kawai, G., Ha, J-M., Oka, T., Kawai, S., Miyake, T., Fuwa, T. and Miyazawa, T. (1988) "Biosynthesis of a protein containing a nanoprotein amino acid by Escherichia coli: L-2 aminohexonoic acid at position 21 in human epidermal growth factor", Pmc. Natl Acad. Sci. USA 85, 6237-6241.
  • Lazar, E., Watanabe, S., Dalton, S. and Sporn, M.B. (1988) "Transforming growth factor a: mutation of asparatic acid 47 and leucine 48 results in different biological activities", MoI. Cell Biol. 87, 1247-1252.
  • Louie, G.V., Yang, W., Bowman, M.E. and Choe, S. (1997) "Crystal structure of the complex of diphtheria toxin with an extracellular fragment of its receptor", Mol. Cell 1, 67-78.
  • Lu, H.S., Chai, J.J., Li, M., Huang, B.R., He, C.H. and Bi, R.C. (2001) "Crystal structure of human epidermal growth factor and its dimerization", J. BioL Chem. 276, 34913-34917.
  • Marquardt, H., Hunkapiller, M.W., Hood, L.E. and Tordaro, G.I. (1984) "Rat transforming growth factor type 1: structure and relation to epidermal growth factor", Science 223, 1079-1082.
  • Montelione, G.T., Wuthrich, K., Nice, E.C., Burgess, A. W. and Scheraga, H.A. (1986) "Identification of anti-parallel ß-sheet conformations in the solution structure of murine growth factor by proton magnetic resonance", Proc. Natl. Acad. Sci. USA 83, 8594-8598.
  • Montelione, G.T., Wuthrich, K., Nice, E.C., Burgess, A.W. and Scheraga, H.A. (1987) "Solution structure of murine epidermal growth factor: determination of the polypeptide backbone chain-fold by nuclear magnetic resonance and distance geometry", Proc. Natl. Acad. Sci. USA 84, 5226-5230.
  • Montelione, G.T., Wuthrich, K., Burgess, A.W., Nice, E.C., Wagner, G., Gibson, K.D. and Scheraga, H.A. (1992) "Solution structure of murine epidermal growth factor determined by NMR spectroscopy and refined by energy minimization with restraints", Biochemistry 31, 236-249.
  • Morihara, K. (1990) "Enzymatic semisynthesis of human insulin: an update", J. MoL Recognit. 3, 181-186.
  • Moy, F.J., Scheraga, H.A., Liu, J-F., Wu, R. and Montelione, G.T. (1989) "Conformational characterization of a single-site mutant of murine epidermal growth factor (EGF) by 1H NMR provides evidence that leucine-47 involved in the interactions with the EGF receptor", Proc. Natl Acad, Sci. USA 86, 9836-9840.
  • Mullis, K.B. and Faloona, F.A. (1987) "Specific synthesis of DNA in vitro via a polymerase-catalyzed chain reaction", Methods Emzymol. 155, 335-350.
  • Nagata, K., Kbhda, D., Harnaka, H., Ichikawa, S., Matsuda, S., Yamamoto, T., Suzuki, A. and Inagaki, F. (1994) "Solution structure of the epidermal growth factor-like domain of heregulin-alpha, a ligand for p180erbB-4", EMBO J. 13, 3517-3523.
  • Nice, E.C. (1990) "Micropreparative LC of proteins", Nature 348, 462-463.
  • Nice, E.C., Grego, B. and Simpson, R.I. (1985) "Application of short microbore HPLC 'guard' columns for the preparation of samples for protein microsequencing", Biochem. Int. 11, 187-195.
  • Nice, E.C., Fabri, L., Whitehead, R.H., lames, R., Simpson, R.J. and Burgess, A.W. (1991) "The major colonic cell mitogen extractable from colonic mucosa is an N-terminally extended form of basic fibroblast growth factor", J. Biol. Chem. 266, 1-6.
  • Nice, E.C., Fabri, L., Hammacher, A., Andersson, K. and Hellman, U. (1993) "Micropreparative ion exchange HPLC: applications to microsequences analysis", Biomed Chromatogr. 7, 104-111.
  • Offord, R.E. (1985) "Semisynthetic peptides and proteins", In: Deber, C.M., Hruby, V.J. and Kopple, K.D., eds, Proceedings of the Ninth American Peptide Symposium (Pierce Chemical Company, Rockford, USA), pp 325-362.
  • Ray, P., Moy, F.I., Montelione, G.T., Liu, J-F., Narang, S.A., Scheraga, H.A. and Wu, R. (1988) "Structure-function studies of murine epidermal growth factor: expression and site-directed mutagenesis of epidermal growth factor gene", Biochemistry 27, 7289-7295.
  • Reisner, A.H. (1985) "Similarity between the vaccina virus 19K early protein and epidermal growth factor", Nature 313, 801-803.
  • Saiki, R.K., Gelfand, D.H., Stoffel, S., Scharf, S.J., Higuchi, R., Horn, G.T., Mullis, K.B. and Erlich, H.A. (1988) "Primer-directed enzymatic amplification of DNA with a thermostable DNA polymerase", Science 239, 487-491.
  • Sakina, K., Kawazura, K. and Morihara, K. (1988) "Enzymatic synthesis of delta sleep inducing peptide", Int. J. Pept. Protein Res. 31, 245-252.
  • Sarin, V.K., Kent, S.B.H., Tam, J.P. and Merrifield, R.B. (1981) "Quantitative monitoring of solid-phase peptide synthesis by the ninhydrin reaction", Anal. Biochem. 117, 147-157.
  • Sasada, R., Ono, Y., Taniyama, Y., Shing, Y, Folkman, I. and Igarashi, K. (1993) "Cloning and expression of cDNA encoding human betacellulin, a new member of the EGF family", Biochem. Biophys. Res. Commun. 15, 1173-1179.
  • Savage, Jr, C.R. and Cohen, S. (1973) "Proliferation of corneal epithelium induced by epidermal growth factor", Exp. Eye Res. 15, 361-366.
  • Savage, C.R., Inagami, T. and Cohen, S. (1972) "The primary structure of epidermal growth factor", J. Biol. Chem. 247, 7612-7621.
  • Shoyab, M., Plowman, G.D., McDonald, V.L., Bradley, J.G. and Todaro, G.J. (1989) "Structure and function of human amphiregulin: a member of the epidermal growth factor family", Science 243, 1074-1076.
  • Simpson, R.J., Smith, I.A., Moritz, R.L., O'Hare, M.J., Rudland, P.S., Morrison, J.R., Lloyd, C.J., Grego, B., Burgess, A.W. and Nice, E.C. (1985) "Rat epidermal growth factor: complete amino acid sequence", Eur. J. Biochem. 153, 629-637.
  • Strachan, L., Murison, J.G., Prestidge, R.L., Sleeman, M.A., Watson, I.D. and Kumble, K.D. (2001) "Cloning and biological activity of epigen, a novel member of the epidermal growth factor superfamily", J. Biol Chem. 276, 18265-18271.
  • Sumi, S-L, Hasegawa, A., Yagi, S., Miyoshi, K., Kanezawa, A., Nakagawa, S. and Suzuki, M. (1985) "Overproduction of human epidermal growth factor/urogastrone in Escherichia call and demonstration of its full biological activities", J. Biotechnol. 2, 59-74.
  • Toyoda, H., Komurasak, T., Uchida, D., Takayama, Y, Isobe, T., Okuyama, T. and Hanada, K. (1995) "Epiregulin. A novel epidermal growth factor with mitogenic activity for rat primary hepatocytes", J. Biol Chem. 270, 7495-7500.
  • Upton, C., Macen, J.L. and McFadden, G. (1987) "Mapping and sequencing of gene from myxoma virus that is related to those encoding epidermal growth factor and transforming growth factor a", J. Virol. 61, 1271-1275.
  • Walker, F., Nice, E., Fabri, L., Moy, F.J., Liu, J.F., Wu, R., Scheraga, H.A. and Burgess, A.W. (1990) "Resistance to receptor-mediated degradation of a murine epidermal growth factor analogue (EGF-Val-47) potentiates its mitogenic activity", Biochemistry 29, 10635-10640.
  • Weaver, L.T. and Walker, WA. (1988) "Epidermal growth factor and the developing human gut", Gastroenterology 94, 845-847.
  • Yarden, Y, Schreiber, A.B. and Schlessinger, J. (1982) "A non-mitogenic analogue of epidermal growth factor induces early responses medicated by epidermal growth factor", J. Cell. Biol. 92, 687-693.
  • Zhang, Y.S. (1983) "Enzymatic synthesis of proteins and peptides", Trends Biochem. Sci. 8, 16-17.

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