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DOI: 10.1055/s-2006-941573
You Are Sitting on a Gold Mine!
Publikationsverlauf
Publikationsdatum:
22. Mai 2006 (online)
Abstract
The synthesis of peptides heavily based on Cα-tetrasubstituted α-amino acids is a rather difficult task as the reactivity of these building blocks in amide bond formation is generally poor, which primarily results from the severe steric hindrance of the α-amino functionality. Nevertheless, such a synthetic approach is very relevant in view of the current extensive utilization of these peptides as membrane-active, antimicrobial, compounds and conformationally restricted, tunable, spacers and templates in modern organic and physical chemistry investigations. In this Account we discuss new mechanistic information, drawbacks, improvements, and successful results published over the years by a number of research groups with special emphasis on the problems encountered and (often) solved in our own journey through this fascinating field.
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1 Introduction
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2 Work on Aib Peptides before 1980
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2.1 Synthesis
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2.2 Conformation
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3 Synthetic and Structural Work on Peptides Based on Aib and Related Amino Acids since 1980
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4 Structural Work on Derivatives of Aib and Related Amino Acids
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5 Conclusions and Outlook
Key words
amino acids - chirality - helical structures - peptides - steric hindrance
- 1 All scientific presentations at the Symposium were published in: Biopolymers 1983, 22: issue 1
- 2
Burgess AW.Leach SJ. Biopolymers 1973, 12: 2599 - 3
Levene PA.Steiger RE. J. Biol. Chem. 1931, 93: 581 - 4
Mohr E. J. Prakt. Chem. 1910, 81: 49 - 5
Kenner GW.Sheppard RC. Nature (London) 1958, 181: 48 - 6
Meyer CE.Reusser F. Experientia 1967, 23: 85 - 7
Benedetti E.Bavoso A.Di Blasio B.Pavone V.Pedone C.Toniolo C.Bonora GM. Proc. Natl. Acad. Sci. U.S.A. 1982, 79: 7951 -
8a
Leplawy MT.Jones DS.Kenner GW.Sheppard RC. Tetrahedron 1960, 11: 39 -
8b
Jones DS.Kenner GW.Preston J.Sheppard RC. J. Chem. Soc. 1965, 6227 -
9a
McGahren WJ.Goodman M. Tetrahedron 1967, 23: 2017 -
9b
Goodman M.McGahren WJ. Tetrahedron 1967, 23: 2031 -
10a
Crisma M.Valle G.Moretto V.Formaggio F.Toniolo C. Pept. Res. 1995, 8: 187 -
10b
Toniolo C.Crisma M.Formaggio F. Biopolymers 1996, 40: 627 ; and references therein -
10c
Crisma M.Moretto V.Valle G.Formaggio F.Toniolo C. Int. J. Pept. Protein Res. 1993, 42: 378 -
10d
Valle G.Toniolo C.Jung G. Liebigs Ann. Chem. 1986, 1809 -
10e
Crisma M.Formaggio F.Valle G.Toniolo C.Saviano M.Iacovino R.Zaccaro L.Benedetti E. Biopolymers 1997, 42: 1 -
10f
Crisma M.Valle G.Formaggio F.Toniolo C.Kamphuis J. Z. Kristallogr. 1995, 210: 634 -
10g
Valle G.Crisma M.Formaggio F.Toniolo C.Redlinski A.Kaczmarek K.Leplawy MT. Z. Kristallogr. 1992, 199: 229 -
10h
Bosch R.Jung G.Winter W. Acta Crystallogr., Sect. C 1983, 39: 1089 -
10i
Crisma M.Valle G.Moretto V.Formaggio F.Toniolo C.Albericio F. Lett. Pept. Sci. 1998, 5: 247 -
10j
Toniolo C.Bonora GM.Crisma M.Benedetti E.Bavoso A.Di Blasio B.Pavone V.Pedone C. Int. J. Pept. Protein Res. 1983, 22: 603 -
10k
Formaggio F.Crisma M.Bonora GM.Pantano M.Valle G.Toniolo C.Aubry A.Bayeul D.Kamphuis J. Pept. Res. 1995, 8: 6 -
11a
Marshall G. In Intra-Science Chemistry Reports Vol. 5:Karasch N. Gordon and Breach; New York: 1971. p.305 -
11b
Ramachandran GN.Chandrasekharan R. In Progress in Peptide Research Vol. II:Lande S. Gordon and Breach; New York: 1972. p.195 -
11c
Venkataram Prasad BV.Sasisekharan V. Macromolecules 1979, 12: 1107 - 12
Toniolo C.Benedetti E. Trends Biochem. Sci. 1991, 16: 350 - 13
Beesley RM.Ingold CK.Thorpe JF. J. Chem. Soc. 1915, 105: 1080 -
14a
Shamala N.Nagaraj R.Balaram P. J. Chem. Soc., Chem. Commun. 1978, 996 -
14b
Smith GD.Duax WL.Czerwinski EW.Kendrick NE.Marshall GR.Mathews FS. In PeptidesGoodman M.Meienhofer J. Wiley; New York: 1979. p.277 -
14c
Shamala N.Nagaraj R.Balaram P. Biochim. Biophys. Res. Commun. 1977, 79: 292 -
15a
Venkatachalam CM. Biopolymers 1968, 6: 1425 -
15b
Toniolo C. CRC Crit. Rev. Biochem. 1980, 9: 1 -
15c
Rose GD.Gierasch LM.Smith JA. Adv. Protein Chem. 1985, 37: 1 -
16a
Nagaraj R.Balaram P. Acc. Chem. Res. 1981, 14: 356 -
16b
Sansom MSP. Prog. Biophys. Mol. Biol. 1991, 55: 139 -
17a
Benedetti E.Bavoso A.Di Blasio B.Pavone V.Pedone C.Crisma M.Bonora GM.Toniolo C. J. Am. Chem. Soc. 1982, 104: 2437 -
17b
Valle G.Formaggio F.Crisma M.Bonora GM.Toniolo C.Bavoso A.Benedetti E.Di Blasio B.Pavone V.Pedone C. J. Chem. Soc., Perkin Trans. 2 1986, 1371 -
17c
Toniolo C.Benedetti E. Macromolecules 1991, 24: 4004 -
17d
Toniolo C.Crisma M.Formaggio F.Valle G.Cavicchioni G.Précigoux G.Aubry A.Kamphuis J. Biopolymers 1993, 33: 1061 -
17e
Toniolo C.Crisma M.Formaggio F.Peggion C. Pept. Sci. 2001, 60: 396 ; and references therein - 18
Goodman M.Toniolo C.Pallai P. In Forum PeptidesCastro B.Martinez J. Dohr; Nancy: 1985. p.146 - 19
König W.Geiger R. Chem. Ber. 1970, 103: 788 - 20
Formaggio F.Broxterman QB.Toniolo C. In Houben-Weyl: Methods of Organic Chemistry Vol. E22c:Goodman M.Felix A.Moroder L.Toniolo C. Thieme; Stuttgart: 2003. p.292 - 21
Venkatachalapathi YV.Nair CMK.Vijayan M.Balaram P. Biopolymers 1981, 20: 1123 - 22
Brückner H.Currle M. In Second Forum PeptidesAubry A.Marraud M.Vitoux B. Libbey Eurotext; London: 1989. p.251 -
23a
Kaminski Z.Leplawy MT.Olma A.Redlinski A. In Peptides 1980. Proceedings of the 16th European Peptide SymposiumBrunfeldt K. Scriptor; Copenhagen: 1981. p.201 -
23b
Leplawy MT.Kaczmarek K.Redlinski A. In Peptides: Chemistry and BiologyMarshall GR. ESCOM; Leiden: 1988. p.239 -
24a
Hardy PM.Lingham IN. Int. J. Pept. Protein Res. 1983, 21: 392 -
24b
Hardy PM.Lingham IN. Int. J. Pept. Protein Res. 1983, 21: 406 -
25a
Benedetti E.Toniolo C.Hardy P.Barone V.Bavoso A.Di Blasio B.Grimaldi P.Lelj F.Pavone V.Pedone C.Bonora GM.Lingham I. J. Am. Chem. Soc. 1984, 106: 8146 -
25b
Benedetti E.Barone V.Bavoso A.Di Blasio B.Lelj F.Pavone V.Pedone C.Bonora GM.Toniolo C.Leplawy MT.Kaczmarek K.Redlinski AS. Biopolymers 1988, 27: 357 - 26
Valle G.Crisma M.Bonora GM.Toniolo C.Lelj F.Barone V.Fraternali F.Hardy PM.Langran-Goldsmith A.Maia HLS. J. Chem. Soc., Perkin Trans. 2 1990, 1481 - 27
Fu Y.Hammer RP. Org. Lett. 2002, 4: 237 -
28a
Crisma M.Valle G.Bonora GM.De Menego E.Toniolo C.Lelj F.Barone V.Fraternali F. Biopolymers 1990, 30: 1 -
28b
Hohenlohe-Oehringen K. Monatsh. Chem. 1962, 93: 639 -
28c
Meldal M.Juliano MA.Jansson AM. Tetrahedron Lett. 1997, 38: 2531 -
28d
Grzegorzewska U.Kaminski ZJ.Leplawy MT. Bull. Acad. Pol. Sci. 1974, 22: 679 -
28e
Yamada T.Omote T.Yamanaka Y.Miyazawa T.Kuwata S. Synthesis 1998, 991 -
28f
Pavone V.Lombardi A.Saviano M.De Simone G.Nastri F.Maglio O.Omote Y.Yamanaka Y.Yamada T. Biopolymers 2000, 53: 161 - 29
Di Blasio B.Pavone V.Saviano M.Lombardi A.Nastri F.Pedone C.Benedetti E.Anzolin M.Toniolo C. J. Am. Chem. Soc. 1992, 114: 6273 -
30a
Moretto V.Valle G.Crisma M.Bonora GM.Toniolo C. Int. J. Biol. Macromol. 1992, 14: 177 -
30b
Spencer JR.Antonenko VV.Delaet NGJ.Goodman M. Int. J. Pept. Protein Res. 1992, 40: 282 -
30c
Suresh Babu VV.Vasanthakumar G.-R.Tantry SJ. Tetrahedron Lett. 2005, 46: 4099 -
30d
Carpino LA.Ionescu D.El-Faham A.Henklein P.Wenschuh H.Bienert M.Beyermann M. Tetrahedron Lett. 1998, 39: 241 -
31a
Kruizinga WH.Bolster J.Kellogg RM.Kamphuis J.Boesten WHJ.Meijer EM.Schoemaker HE. J. Org. Chem. 1988, 53: 1826 -
31b
Sonke Th.Kaptein B.Boesten WHJ.Broxterman QB.Schoemaker HE.Kamphuis J.Formaggio F.Toniolo C.Rutjes FPJT. In Stereoselective BiocatalysisPatel RN. Dekker; New York: 1999. p.23 - 32
Carpino LA. J. Am. Chem. Soc. 1993, 115: 4397 -
33a
Polese A.Formaggio F.Crisma M.Valle G.Toniolo C.Bonora GM.Broxterman QB.Kamphuis J. Chem. Eur. J. 1996, 2: 1104 -
33b
Formaggio F.Moretto V.Crisma M.Toniolo C.Kaptein B.Broxterman QB. J. Pept. Res. 2004, 63: 161 -
33c
Toniolo C.Polese A.Formaggio F.Crisma M.Kamphuis J. J. Am. Chem. Soc. 1996, 118: 2744 -
33d
Yoder G.Polese A.Silva RAGD.Formaggio F.Crisma M.Broxterman QB.Kamphuis J.Toniolo C.Keiderling TA. J. Am. Chem. Soc. 1997, 119: 10278 -
34a
Carpino LA.Sadat-Aalaee D.Chao HG.DeSelms RH. J. Am. Chem. Soc. 1990, 112: 9651 -
34b
Fiammengo R.Licini G.Nicotra A.Modena G.Pasquato L.Scrimin P.Broxterman QB.Kaptein B. J. Org. Chem. 2001, 66: 5905 -
34c
Carpino LA.Beyermann M.Wenschuh H.Bienert M. Acc. Chem. Res. 1996, 29: 268 -
35a
Dal Pozzo A.Ni M.Muzi L.Caporale A.de Castiglione R.Kaptein B.Broxterman QB.Formaggio F. J. Org. Chem. 2002, 67: 6372 -
35b
Ni M.Esposito E.Kaptein B.Broxterman QB.Dal Pozzo A. Tetrahedron Lett. 2005, 46: 6369 -
36a
Imawaka N.Tanaka M.Suemune H. Helv. Chim. Acta 2000, 83: 2823 -
36b
Toniolo, C.; Formaggio, F.; Crisma, M.; Moretto, A.; Kaptein, B.; Broxterman, Q. B. manuscript in preparation.
-
37a
Nakaie CR.Goissis G.Schreier S.Paiva ACM. Braz. J. Med. Biol. Res. 1981, 14: 173 -
37b
Toniolo C.Crisma M.Formaggio F. Pept. Sci. 1998, 47: 153 -
37c
Toniolo C.Valente E.Formaggio F.Crisma M.Pilloni G.Corvaja C.Toffoletti A.Martinez GV.Hanson MP.Millhauser GL.George C.Flippen-Anderson JL. J. Pept. Sci. 1995, 1: 45 -
37d
Crisma M.Deschamps JR.George C.Flippen-Anderson JL.Kaptein B.Broxterman QB.Moretto A.Oancea S.Jost M.Formaggio F.Toniolo C. J. Pept. Res. 2005, 65: 564 -
37e
Marchetto R.Schreier S.Nakaie CR. J. Am. Chem. Soc. 1993, 115: 11042 -
37f
Martin L.Ivancich A.Vita C.Formaggio F.Toniolo C. J. Pept. Res. 2001, 58: 424 -
37g
Crisma M.Valle G.Formaggio F.Toniolo C.Bagno A. J. Am. Chem. Soc. 1997, 119: 4136 -
38a
Monaco V.Formaggio F.Crisma M.Toniolo C.Hanson P.Millhauser GL. Biopolymers 1999, 50: 239 -
38b
Toniolo C.Crisma M.Formaggio F.Peggion C.Broxterman QB.Kaptein B. J. Inclusion Phenom. Macrocycl. Chem. 2005, 51: 121 ; and references therein -
39a
Antonello S.Formaggio F.Moretto A.Toniolo C.Maran F. J. Am. Chem. Soc. 2003, 125: 2874 -
39b
Moretto A.De Zotti M.Scipionato L.Formaggio F.Crisma M.Toniolo C.Antonello S.Maran F.Broxterman QB. Helv. Chim. Acta 2002, 85: 3099 -
39c
Formaggio F.Crisma M.Scipionato L.Antonello S.Maran F.Toniolo C. Org. Lett. 2004, 6: 2753 -
40a
Peggion C.Coin I.Toniolo C. Pept. Sci. 2004, 76: 485 ; and references therein -
40b
Toniolo C.Crisma M.Formaggio F.Peggion C.Epand RF.Epand RM. Cell. Mol. Life Sci. 2001, 58: 1179 -
41a
Fuller WD.Cohen MP.Shabankareh M.Blair RK.Goodman M.Naider F. J. Am. Chem. Soc. 1990, 112: 7414 -
41b
Fuller WD.Goodman M.Naider FR.Zhu YF. Biopolymers (Pept. Sci.) 1996, 40: 183 - 42
Bodanszky M.Fink ML.Funk KW.Kondo M.Lin CY.Bodanszky A. J. Am. Chem. Soc. 1974, 96: 2234 -
43a
Barlos K.Papaioannou D.Voliotis S.Prewo R.Bieri JH. J. Org. Chem. 1985, 50: 696 -
43b
Sliedregt KM.Schouten A.Kroon J.Liskamp RMJ. Tetrahedron Lett. 1996, 37: 4237 - 44
König W.Geiger R. Chem. Ber. 1970, 103: 2024 -
45a
Fujiwara H.van der Veen JM. J. Chem. Soc., Perkin Trans. 2 1979, 659 -
45b
Madison V.Young PE.Blout ER. J. Am. Chem. Soc. 1976, 98: 5358 - 46
Antonovics I.Heard AL.Hugo J.Williams MW.Young GT. In Peptides: Proceedings of the 6th European Peptide SymposiumZervas L. Pergamon Press; Oxford: 1966. p.121