Abstract
For more than a century and a half, organic chemists have been investigating the complex structures found in living organisms. Among these are the nitrogen-containing substances of high molecular weight known as proteins.
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References
Hofmeiser F (1902): Ergeb Physiol Biol Chem Exp Pharmacol 1:759
Fischer E (1906): Ber dtSch Chem Ges 39:530
Finn FM, Hofmann K (1976): In: The Proteins, Vol. 11, Neurath H, Hill RL, eds. New York: Academic Press
Bodanszky M, Bodanszky A (1984): The Practice of Peptide Synthesis. Berlin:Springer Verlag
Merrifìeld RB (1963): J Am Chem Soc 85:2149
Erickson BW, Merrifìeld RB (1976): In: The Proteins, Vol. 11, Neurath H, Hill RL, eds. New York: Academic Press
Barany G, Merrifìeld RB (1979): In: The Peptides, Vol. 2, Gross E, Meienhofer J, eds. New York: Academic Press
Barney G, Kneib-Cordonier N, Mullen DG (1988): In: Encyclopedia of Polymer Science and Engineering, Vol. 12, Kroschwitz JT, ed. New York: John Wiley
Field GB, Noble RL (1990): J Pep Protein Res 35:161–214
Geiger R, Konig W (1981): In: The Peptides: Analysis, Synthesis and Biology, Vol. 3, Gross E, Meienhofer J, eds. New York: Academic Press
Young GT (1981): Biopolymers 20:1805
Carpino LA (1973): Acc Chem Res 6:191
Fruton JS (1982): Trends Biochem Sci 7:37
Calpin IJ (1984): In: Amino Acids Peptides and Proteins, Vols 15,16, Jones JH, ed. London: Royal Society of Chemistry
Shotter C (1888): Chem Ber 21:2235
Baumann E (1886): Chem Ber 19:3218
Sheeham JC, Haung DH (1917): J Am Chem Soc 111:190
Tesh HW, Schulz RC (1981): Makromol Chem 182:2981
Hofmann K, Yajima H (1961): J Am Chem Soc 83:2289
Weygand F (1954): Chem Zlg 78:480
Fones WS, Lee MI (1954): J Biol Chem 210:277
Weygand F, Geiger R (1956): Chem Ber 89:647
Sheehan JC, Goodman M, Hess GP (1956): J Am Chem Soc 78:1367
Kisfaludy L, Dualszky S (1960): Acta Chim Hung 24:301
Bergmann M, Zervas L (1932): Chem Ber 65:1192
Ben Ishai D, Berger A (1952): J Org Chem 17:1564
Anderson GW, Blodinger J, Welcher AD (1952): J Am Chem Soc 74:5304
Udenfriend S, Meienhofer J (1987): In: The Peptides, Vol. 9, San Diego, CA: Academic Press
Khan SA, Merkel GJ, Bekeer JM, Naider F (1981): Int J Pept Protein Res 17:219
Anwer MK, Spatola AF (1981): Tetrahedron Lett 4369
Anwer MK, Spatola AF (1980): Synthesis 929
Colombo R, Hoppe-Seylers Z (1981): Physiol Chem 362:1393
Blaha K, Rudinger J (1965): Coll Czech Chem Comm 30:585–599
Carpino LA (1957): J Am Chem Soc 79:98
McKay FC, Albertson NF (1957): J Chem Soc 79:4686
Anderson GW, McGregor AC (1957): J Am Chem Soc 79:6180
Alakhou YB, Kiryushkin AA, Lipkin VM, Millne GW (1970): A Chem Comm 406
Kisfaludy L, Geiger R (1981): In: The Peptides, Analysis, Synthesis, Biology, Vol. 3, Gross E, Meienhofer J, eds. New York: Academic Press
Tarbell DS, Vamamoto Y, Pope BM (1972): Proc Natl Acad Sci USA 64:730
Moroder L, Hallett A, Wunsch E, Keller O, Wersin G (1976): Hoppe-Seyler’s Z Physiol Chem 357:1651
Tarbell DS, Insalaco MA (1968): Proc Natl Acad Sci USA 57:233
Sieber P, Iselin B (1968): Helv Chem Acta 51:614–622
Wang SS, Merrifield RB (1964): Int J Pept Protein Res 1:235
Feinberg RS, Merrifield RB (1972): Tetrahedron 28:5865
Schnabel E, Schmidt G, Klauke E (1971): Justus Liebigs Ann Chem 743:69
Carpino LA, Han GY (1970): J Amer Chem Soc 92:5748
Carpino LA, Han GY (1972): J Org Chem 37:3404
Kadar AT, Stirling CJM (1962): Proc Chem Soc 363
Udenfriend S, Meienhofer J (1987): In: The Peptide, Vol. 9, San Diego, CA: Academic Press
Sigler GF, Fuller WD, Chaturredi NC, Goodman M, Verlander M (1983): Biopolymers 22:2157
Tessier M, Albericio F, Fedroso E, Grandas A, Eritza R, Giralt E, Granier C, Van Rietschoten J (1983): Int J Pept Protein Res 22:125
Lapatsanis L, Milias G, Froussions K, Koloros M (1983): Synthesis: 671
Bolin DR (1984): European Patent Application EP 129, 075. (1985): Chem Abst 102:204290
Atherton E, Fox H, Harkiss D, Sheppard RC (1978): J Chem Soc Chem Comm 539
Rosamund JD, Ferger MF (1976): J Med Chem 19:873
Bodanszky M (1968): In: Peptides 1968, Bricas E, ed. North-Holland Pub Amsterdam: P. 150
Kopple KD, Saito T, Ohnishi M (1969): J Org Chem 34:1631
Natarajan S, Bodanszky M (1976): J Org Chem 41:1269
Roeske RW (1959): Chem Ind (London): 1121
Roeske RW (1963): J Org Chem 28:1251
Anderson GW, Callaham FM (1960): J Am Chem Soc 82:3359
Chimiak A, Lolasa T, Biernat JF (1972): Z Chem 12:264
Wang S-S, Gisin BF, Winter DP, Makofske R, Kulesha TD, Tzougraki C, Meienhofer J (1977): J Org Chem 42:1286
Shahan JC, Daves GD (1964): J Org Chem 29:2006
Ledger R, Stewart FHC (1965): Aus J Chem 18:1477
Hendrickson JB, Kendall C (1970): Tetrahedron Lett: 343
Carpino LA, Chao H-G, Ghassemi S, Mansour EME, Riemer C, Warrass R, Sadat-Aalee D, Truran GA, Imazumi H, Ayman El-F, Ionescu D, Ismail M, Kowaleski TL, Han CH (1995): J Org Chem 60:7718
Fischer E (1903): Ber dtsch Chem Ges 36:2094
Jones DS, Kenner GW, Sheppard RC (1965): J Chem Soc: 4393
Curtius T (1902): Ber dtsch Chem Ges 35:3226
Klausner YS, Bodanszky M (1974): Synthesis: 549
Wünsch E, Wendlberger G (1967): Chem Ber 100:160–172
Chen-Francis MF, Kuroda K, Benoiton NL (1978): Syn Comm: 928–929
Paquet A, Chen-Francis MF, Benoiton NL (1984): Can J Chem 62:1335–1338
Schröder E, Lubke K, eds. and Auts (1965): In: The Peptides, Vol. 1. NewYork: Academic Press
Fairweather R, Jones JH (1972): J Chem Soc Perkin Trans 1:1908
Chen-Francis MF, Benoiton N (1987): Can J Chem 65:619–625
Gross E, Meienhofer J (1979): In: The Peptides, Vol. 1, New York: Academic Press
Gross E, Meienhofer J (1979): In: The Peptides, Vol. 1, New York: Academic Press
Leuchs H (1906): Ber dtsch Chem Ges 69:857
Cohen BJ (1979): Ph.D. Dissertation. Rebovot, Israel: Weizmann Institute of Science
Pass S, Amit B, Patchornik A (1981): J Am Chem Soc 103:7674
Sadat-Aalaee SY (1990): Ph.D. Dissertation Amherst, MA: University of Massachusetts
Beyermann M, Bienert M, Niedrich H, Carpino LA, Sadat-Aalaee D (1990): J Org Chem 55:721
Carpino LA, Chao HG, Beyermann M, Bienert M (1991): J Org Chem 56:2635
Carpino LA, Mansour, El-Sayed ME, Sadat-Aalaee D (1991): J Org Chem 56:2611
Carpino LA, Mansour, EME (1992): J Org Chem 57:6371
Carpino LA, Mansour, EME, Ayman E-F (1993): J Org Chem 58:4162
Carpino LA, Sadat-Aalaee D, Chao HG, DeSelms RH (1990): J Am Chem Soc 112:9651
Bertho J-N, Loffet A, Pinel C, Reather F, Sennyey G (1991): Tetrahedron Lett 32:1303–1306
Wenschuh H, Beyermann M, Krause E, Brudel M, Winter R, SchĂĽmann M, Carpino LA, Bienert M (1994): J Org Chem 59:3275
Wenschuh H, Beyermann M, Krause E, Carpino LA, Bienert M (1993): Tetrahedron Lett 34:3733
Sieber P, Riniker B, Brugger M, Kamber B, Rittel W (1970): Helv Chim Acta 53:2135
Bodanszky M (1984): Principles of Peptide Synthesis. Berlin Heidelberg
Hasimoto Y, Imanishi Y (1981): BioPolymers 20:488; 20:507
Oya M, Takahishi TJ (1982): Polym Sci Polym Chem Ed 20:529
Atreyi M, Rao VR, Kumar S (1983): BioPolymers 22:747
Mobashary S, Johnston M (1985): J Org Chem 50:2200
Daly WH, Poché D (1988): Tetrahedron Lett 29:5859
Bartlett PD, Jones RH (1957): J Am Chem Soc 79:2153
Grant NH, Alburn HE (1964): J Am Chem Soc 86:3870
Fuller WD, Cohen MP, Shabankareh M, Blair RK, Goodman M, Naider FR (1990): J Am Chem Soc 112:7414
Xue C-B, Naider F (1993): J Org Chem 58:350–355
Spencer JR, Antonenko VV, Delaet NGJ, Goodman M (1992): Int J Pep Protein Res 40:282
Swain PA, Anderson BL, Goodman M, Fuller D (1993): Peptide Res 6:147
Hudson D (1990): Peptide Res 3:51–55
Sheehan JC, Hess GP (1955): J Am Chem Soc 77:1067
König W, Geiger R (1970): Chem Ber 103:2024, 2034
König W, Geiger R (1973): Chem Ber 106:3626–3635
Shioiri T, Yamada S-I (1974): Chem Pharm Bull 22:849
Ibid 855
Ibid 859
Shioiri T, Yokoyama Y, Kasai Y, Yamada S (1976): Tetrahedron 32:2211
Yamada S, Kasai Y, Shioiri T (1973): Tetrahedron Lett: 1595
Yamada S, Ikota N, Shioiri T, Tachibana S (1974): J Am Chem Soc 97:7174
Yamada Y, Rishi S, Shioiri T, Yamada S (1977): Chem Pharm Bull 25:224
Castro B, Domoy JR, Evin G, Selve C (1975): Tetrahedron Lett 14:1219
Audousset-Puech MD, Dufuor M, Kevran A, Jarousse C, Castro B, Bataille D, Martinez J (1986): FEBS Lett 200:181
Fournier A, Wang CT, Felix AM (1988): Int J Pept Protein Res 31:86–97
Kim MH, Patel DV (1994): Tetrahedron Lett 35:5603
Felix AM, Wang C-T, Heimer EP, Fournier A (1988): Int J Pep Protein Res 31:231
Coste J, Le-Nguyen D, Castro B (1900): Tetrahedron Lett 31:205
Dourtoglou V, Gross B, Lambropoulou V, Zioudrou C (1984): Synthesis: 572–574
Carpino LA (1993): J Am Chem Soc 115:4397
Carpino LA, Ayman El-Faham A, Minor CA, Albericio F (1994): J Chem Soc Chem Commun 201
Carpino LA, Eyman El-Faham A (1995): J Org Chem 60:3561
Carpino LA, Eyman El-Faham A (1996): J Am Chem Soc: in press
Mutter M, Hagenmaier H, Beyer E (1971): Angew Chem Int Ed Engl 10:811
Bayer E, Mutter M (1972): Nature 237:512
Nozaki S, Muramatsu I (1982): Bull Chem Soc Jpn 55:2165–2168
Gross E, Meienhofer J (1980): In: The Peptides, Vol. 2. New York: Academic Press
Sheehan JC, Cruickshank PA, Boshart GL (1961): J Org Chem 26:2525
Camble R, Garner R, Young GT (1968): Nature 217:247
Boissonnas RA (1951): Helv Chim Acta 34:874
Wieland T, Bernhard H (1951): Justus Liebig’s Ann Chem 572:190
Vaughan JR (1951): J Am Chem Soc 73:3547
Tilak MA, Hendricks ML, Wedel DS (1972): In: Progress in Peptide Research, Lande S, ed. New York: Gordon & Breach
Bodanszky M, Funk KW, Fink ML (1973): J Org Chem 38:3565–3570
Kisfaludy L, Schön I, Gorog S, Renyei M (1975): J Am Chem Soc 97:5588–5589
Kisfaludy L, Roberts JE, Johnson RH, Mayers GL, Kovacs L (1970): J Org Chem 35:3565
Kovacs J, Mayers RH, Johnson ER, Cover ER, Ghatak UR (1970): J Org Chem 35:1810
Kovacs J, Cover RE, Johnson RH, Kalas TJ, Mayers GL, Roberts JE (1973): J Org Chem 38:2518–2521
Kisfaludy L, Schön I, Szirtes T, Ny-ki O, Low M (1974): Tetrahedron Lett 19:1785–1786
Kisfaludy L, Ny-ki O (1975): Acta Chim Acad Sci Hung 86:343
Kisfaludy L, Schön I (1975): Acta Chim Acad Sci Hung 84:227
Carpino LA, Cohen BJ, Stephens KE, Sadat-Aalaee SY, Tien JH, Langridge DC (1986): J Org Chem 51:3732
Carpino LA, Sadat-Aalaee D, Beyermann M (1990): J Org Chem 55:1673
Wuench E, Wendlberger G (1972): Chem Ber 105:2508–2519
Okada Y, Kawasaki K, Iguchi S, Yagyu M, Yamaji K, Takagi T, Tanizawa O (1981): J Chem Soc Chem Soc Chem Commun 357
Voskuyl-Holtkamp I, Schattenkerk C, Havinga E (1976): Int J Pept Protein Res 8:455
Kuroda H, Chen YN, Watanabe TX, Kimura T, Sakakibara S (1992): Peptide Research 5:265
Nishio H, Kumagaye S, Kurodo H, Chino N, Emura J, Kimura T, Sakakibara S (1992): Peptide Research 5:227
Kubo S, Chino N, Watanabe TX, Kimura T, Sakakibara S (1993): Peptide Research 6:66
Sakakibara S (1995): Biopolymers (PeptSci) 37:17–28
Sarin VK, Kent SBH., Merrifield RB (1980): J Am Chem Soc 102:5463–5470
Arshady R, Atherton E, Clive DLJ, Sheppard RC (1981): J Chem Soc Perkin Trans 1:529–537
Bernatowicz MS, Daniels SB, Coull JM, Kearney T, Neves RS, Coassin PJ, Köster H (1990): In: Current Research in Protein Chemistry; Technique, Structure, and Function, Villafrance JJ, ed. San Diego: Academic Press
Frank R, Döring R (1988): Tetrahedron 44:6031–6040
Lebl M, Eichler J (1989): Peptide Res 2:297–300
Eichler J, Beyermann M, Bienert M (1989): Collect Czech Chem Commun 54:1746–1752
BĂĽttner K, Zahn H, Fisher WH (1988): In: Peptides; Chemistry and Biology Marshall GR, ed. Leiden, The Netherlands: ESCOM
Tregear GW (1972): In: Chemistry and Biology of Peptides, Meienhofer J, ed. Ann Arbor, MI: Ann Arbor Science Publications
Berg RH, Almdal K, Pedersen WB, Holm A, Tarn JP (1989): J Am Chem Soc 111:8024–26
Tam JP, Tjoeng FS, Merrifield RB (1980): Tetrahedron Lett 4935 J Am Chem Soc 102:6117
Tam JP, Dimarchi RD, Merrifield RB (1980): Int J Pept Protein Res 6:412; (1981): Tetrahedron Lett 2851
Andreu D, Merrifield RB, Steiner H, Boman HG (1983): Proc Nat Acad Sci USA 80:6475
Voss C, Dimarchi R, Whitney DB, Tjoeng FS, Merrifield RB, Tam JP (1983): Int J Pept Protein Res 22:204
Udenfriend S, Meienhofer J (1987): In: The Peptides, Vol. 9. San Diego, CA: Academic Press
Kaiser ET, Mihara H, LaForet GA, Kelly JW, Walters L, Findeis MA, Sasaki T (1989): Science 243:187–192
Kneib-Cordonier N, Albericio F, Barany G (1990): Int J Pept Protein Res 35:527–38
Nakagawa SH, Lau HSH, Kézdy FJ, Kaiser ET (1985): J Am Chem Soc 107:7087–7092
Kneib-Cordonier N, Albericio F, Barany G (1990): Int J Pept Protein Res 35:527–38
Grandas A, Albericio F, Josa J, Giralt E, Pedroso E, Sabatier JM, Van Rietschoten J (1989): Tetrahedron 45:4637–48
Barlos K, Gatos D, Schöfer W (1990): Angew Chem Int Ed Engl 30:590
Albericio F, Pons M, Pedroso E, Giralt E (1989): J Org Chem 54:360
Osborn NJ, Robinson A (1993): Tetrahedron 49:2873
Liu Ch-F, Tarn JP (1994): Proc Natl Acad Sci USA 91:6584
Thornton JM (1981): J Mol Biol 151:261–287
Richardson JS (1981): Adv Prot Chem 34:167–339
Sugg EE, Tourwe D, Kazmierski W, Hruby VI, VanDinst G (1988): Int J Pept Protein Res 31:192–200
Albericio F, Granier C, Labbé-Juillié C, Seagar M, Couraud F, Van Rietschoten J (1984): Tetrahedron 40:4313–4326
Verber D, Mikowski JD, Varga SL, Denkewalter RG, Hirschmann R (1972):J Am Chem Soc 94:5456–61
Wade JD, Fitzgerald SP, McDonald MR, McDougall JG, Tregear GW(1986): Biopolymers 25:521–37
Ruiz-Gayo M, Royo M, Fernández I, Albericio F, Giralt E, Pons M (1993): J Org Chem 58:6319–28
Munson MC, Barany G (1993): J Am Chem Soc 115:10203–216
GarcĂa-EcheverrĂa C, Albericio F, Giralt E, Pons M (1993): J Am Chem Soc 115:11663–670
Live DH, Agosta WC, Cowburn D (1977): J Org Chem 42:3556–61
Rivier J, Kaiser F, Galyean R (1978): Biopolymers 17:1927–38
Tam JP, Wu C-R, Liu W, Zhang J-W (1991): J Am Chem Soc 113:6659–6662
Pennington MW, Kern WR, Dunn BM (1990): Peptide Research 3:228–232
Tam JP (1987): Int J Pept Protein Res 29:421–431
Bishop P, Chmielewski J (1992): Tetrahedron Lett 33:6263–66
Bishop P, Jones C, Chmielewski J (1993): Tetrahedron Lett 34:4469–72
Akaji K, Fujino K, Tatsumi T, Kiso Y (1993): J Am Chem Soc 115:11384–392
Inui T, Hagiwara K, Nakajima K, Kimura T, Nakajima T, Sakakibara S (1992): Peptide Resarch 5:140–144
Munson MC, Lebl M, Slaninová J, Barany G (1993): Peptide Research 6:155–159
Barany G, Merrifield RB (1980): In: The Peptides, Analysis, Synthesis, Biology Vol. 2, Gross E, Meienhofer J, eds. New York: Academic Press
Hodges RS, Merrifield RB (1975): Anal Biochem 65:241–72
Arad O, Houghten RA (1990): Peptide Research 3:42–50
Horn M, Novak C (1987): Am Biotech Lab 5:12–21
Reddy MP, Voelker PJ (1985): Int J Pept Protein Res 31:345–348
Krchnäk V, Vágner J, Safár P, Lebl M (1988): Coll Czech Chem Commun 53:2542
Flegel M, Sheppard RC (1990): J Chem Soc Chem Commun: 536
Kaiser E, Colescott RL, Bossinger CD, Cook PI (1970): Anal Biochem 34:595–598
Kaiser E, Bossinger CD, Colescott RL, Olsen DB (1980): Anal Chim Acat 118:144–151
Tam JP, Heath WF, Merrifield RB (1983): J Am Chem Soc 105:6442
Tam JP, Merrifield RB (1987): In: The Peptides, Vol. 9, Undenfriend S, Meienhifer J, eds. New York: Academic Press
Jajima H, Fujii N, Funakoshi S, Watanabe T, Murayama E, Otaka A (1988): Tetrahedron 44:805–819
King DS, Fields CG, Fields GB (1990): Int J Pept Protein Res 36:255–266
Albericio F, Kneib-Cordonier N, Biancalana S, Gera L, Masada RI, Hudson D, Barany G (1990): J Org Chem 55:3730
Sole NA, Barany GJ (1992): J Org Chem 57:5399
Riniker B, Hartmann A (1990): In:Peptides, Chemistry, Structure, and Biology, Rivier JE, Marshall GR, eds. Leiden, The Netherlands: Escom
Chan WC, Bycroft BW (1992): In: 12th American Peptide Symposium Program and Abstracts. Cambridge, MA: Massachusetts Institute of Technology
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Sadat-Aalaee, D. (1997). Chemical Synthesis of Peptides and Polypeptides. In: McGrath, K., Kaplan, D. (eds) Protein-Based Materials. Bioengineering of Materials. Birkhäuser Boston. https://doi.org/10.1007/978-1-4612-4094-5_1
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