Peptide Nanotubes: A Crystallographic Approach
121
Brandl M, Weiss MS, Jabs A, Sühnel J, Hilgenfeld R (2001) C-h· · · π-interactions in proteins. J
Mol Biol 307(1):357–377
Brasun J, Makowski M, Oldziej S, Swiatek-Kozlowska J (2004) Coordination ability of pentapeptides with two dehydro-amino acid residues inserted into their sequences. J Inorg Biochem
98:1391–1398
Broda MA, Siodlak D, Rzeszotarska B (2005) Conformational investigation of alpha, betadehydropeptides. XV: N-acetyl-alpha, beta-dehydroamino acid N ‘N’ dimethylamides: conformational properties from infrared and theoretical studies. J Pept Sci 11:546–555
Bruker (1998) SMART, SAINT, XPREP and SHELXTL. Bruker AXS Inc., 5465 East Cheryl
Parkway, Madison, WI, USA, pp 53711–5373
Chopra NG, Luyken RJ, Cherrey K, Crespi VH, Cohen ML, Louie SG, Zettl A (1995) Boron nitride
nanotubes. Science 269:966–967
DeGrado WF (1988) Design of peptides and proteins. Adv Protein Chem 39:51–124
Dessau RM, Schlenker JL, Higgins JB (1990) Framework topology of aluminophosphate AlPO4-8:
the first 14-ring molecular sieve. Zeolites 10:522–524
Dossena A, Marchelli R, Pochini A (1974) New metabolites of Aspergillus amstelodami related to
the biogenesis of neoechinulin. J Chem Soc Chem Commun 771–772
Engels M, Bashford D, Ghadiri MR (1995) Structure and dynamics of self-assembling peptide
nanotubes and the channel-mediated water organization and self-diffusion. a molecular dynamics
study. J Am Chem Soc 117:9151–9158
English ML, Stammer CH (1978) D-Ala2, zPhe4-methionine enkephalin amide, a dehydropeptide
hormone. Biochem Biophys Res Commun 85(2):780–782
Etter MC, MacDonald JC, Bernstein J (1990) Graph-set analysis of hydrogen-bond patterns in
organic crystals. Acta Crystallogr B 46:256–262
Fei Z, Zhao D, Geldbach TJ, Scopelitti R, Dyson PJ (2005) A synthetic zwitterionic water channel:
characterisation in the solid state by X-ray crystallography and NMR spectroscopy. Angew Chem
Int Ed 44:5720–5725
Fisher GH, Berryer P, Ryan JW, Chauhan VS, Stammer CH (1981) Dehydrophenylalanyl analogs
of bradykinin: synthesis and biological activities. Arch Biochem Biophys 211:269–275
Gazit E (2007) Self-assembled peptide nanostructures: the design of molecular building blocks and
their technological utilization. Chem Soc Rev 36:1263–1269
Ghadiri MR, Granja JR, Milligan RA, McRee DE, Khazanovich N (1993) Self-assembling organic
nanotubes based on a cyclic peptide architecture. Nature 366:324–327
Ghadiri MR, Granja JR, Buehler LK (1994) Artificial transmembrane ion channels from selfassembling peptide nanotubes. Nature 369:301–304
Gorbitz CH (2001) Nanotube formation by hydrophobic dipeptides. Chem Eur J 7:5153–5159
Gorbitz CH (2002a) An exceptionally stable peptide nanotube system with flexible pores. Acta
Crystallogr Sect B 58:849–854
Gorbitz CH (2002b) Beta turns, water cage formation and hydrogen bonding in the structures of
L -valyl- L -phenylalanine. Acta Crystallogr B 58:512–518
Gorbitz CH (2003) Nanotubes from hydrophobic dipeptides: pore size regulation through side chain
substitution. New J Chem 27:1789–1793
Gorbitz CH (2006) The structure of nanotubes formed by diphenylalanine, the core recognition
motif of Alzheimer’s beta-amyloid polypeptide. Chem Commun (Camb) 2332–2334
Görbitz CH (1999) Acta Crystallogr C Cryst Struct Commun 55(12):2171–2177
Gorbitz CH, Nilsen M, Szeto K, Tangen LW (2005) Microporous organic crystals: an unusual case
for L-leucyl-L-serine. Chem Commun 14:4288–4290
Gross E, Morell JL (1967) The presence of dehydroalanine in the antibiotic nisin and its relationship
to activity. J Am Chem Soc 89:2791–2792
Gupta M, Bagaria A, Mishra A, Mathur P, Basu A, Ramakumar S, Chauhan VS (2007) Selfassembly of a dipeptide-containing conformationally restricted dehydrophenylalanine residue to
form ordered nanotubes. Adv Mater 19:858–861
121
Brandl M, Weiss MS, Jabs A, Sühnel J, Hilgenfeld R (2001) C-h· · · π-interactions in proteins. J
Mol Biol 307(1):357–377
Brasun J, Makowski M, Oldziej S, Swiatek-Kozlowska J (2004) Coordination ability of pentapeptides with two dehydro-amino acid residues inserted into their sequences. J Inorg Biochem
98:1391–1398
Broda MA, Siodlak D, Rzeszotarska B (2005) Conformational investigation of alpha, betadehydropeptides. XV: N-acetyl-alpha, beta-dehydroamino acid N ‘N’ dimethylamides: conformational properties from infrared and theoretical studies. J Pept Sci 11:546–555
Bruker (1998) SMART, SAINT, XPREP and SHELXTL. Bruker AXS Inc., 5465 East Cheryl
Parkway, Madison, WI, USA, pp 53711–5373
Chopra NG, Luyken RJ, Cherrey K, Crespi VH, Cohen ML, Louie SG, Zettl A (1995) Boron nitride
nanotubes. Science 269:966–967
DeGrado WF (1988) Design of peptides and proteins. Adv Protein Chem 39:51–124
Dessau RM, Schlenker JL, Higgins JB (1990) Framework topology of aluminophosphate AlPO4-8:
the first 14-ring molecular sieve. Zeolites 10:522–524
Dossena A, Marchelli R, Pochini A (1974) New metabolites of Aspergillus amstelodami related to
the biogenesis of neoechinulin. J Chem Soc Chem Commun 771–772
Engels M, Bashford D, Ghadiri MR (1995) Structure and dynamics of self-assembling peptide
nanotubes and the channel-mediated water organization and self-diffusion. a molecular dynamics
study. J Am Chem Soc 117:9151–9158
English ML, Stammer CH (1978) D-Ala2, zPhe4-methionine enkephalin amide, a dehydropeptide
hormone. Biochem Biophys Res Commun 85(2):780–782
Etter MC, MacDonald JC, Bernstein J (1990) Graph-set analysis of hydrogen-bond patterns in
organic crystals. Acta Crystallogr B 46:256–262
Fei Z, Zhao D, Geldbach TJ, Scopelitti R, Dyson PJ (2005) A synthetic zwitterionic water channel:
characterisation in the solid state by X-ray crystallography and NMR spectroscopy. Angew Chem
Int Ed 44:5720–5725
Fisher GH, Berryer P, Ryan JW, Chauhan VS, Stammer CH (1981) Dehydrophenylalanyl analogs
of bradykinin: synthesis and biological activities. Arch Biochem Biophys 211:269–275
Gazit E (2007) Self-assembled peptide nanostructures: the design of molecular building blocks and
their technological utilization. Chem Soc Rev 36:1263–1269
Ghadiri MR, Granja JR, Milligan RA, McRee DE, Khazanovich N (1993) Self-assembling organic
nanotubes based on a cyclic peptide architecture. Nature 366:324–327
Ghadiri MR, Granja JR, Buehler LK (1994) Artificial transmembrane ion channels from selfassembling peptide nanotubes. Nature 369:301–304
Gorbitz CH (2001) Nanotube formation by hydrophobic dipeptides. Chem Eur J 7:5153–5159
Gorbitz CH (2002a) An exceptionally stable peptide nanotube system with flexible pores. Acta
Crystallogr Sect B 58:849–854
Gorbitz CH (2002b) Beta turns, water cage formation and hydrogen bonding in the structures of
L -valyl- L -phenylalanine. Acta Crystallogr B 58:512–518
Gorbitz CH (2003) Nanotubes from hydrophobic dipeptides: pore size regulation through side chain
substitution. New J Chem 27:1789–1793
Gorbitz CH (2006) The structure of nanotubes formed by diphenylalanine, the core recognition
motif of Alzheimer’s beta-amyloid polypeptide. Chem Commun (Camb) 2332–2334
Görbitz CH (1999) Acta Crystallogr C Cryst Struct Commun 55(12):2171–2177
Gorbitz CH, Nilsen M, Szeto K, Tangen LW (2005) Microporous organic crystals: an unusual case
for L-leucyl-L-serine. Chem Commun 14:4288–4290
Gross E, Morell JL (1967) The presence of dehydroalanine in the antibiotic nisin and its relationship
to activity. J Am Chem Soc 89:2791–2792
Gupta M, Bagaria A, Mishra A, Mathur P, Basu A, Ramakumar S, Chauhan VS (2007) Selfassembly of a dipeptide-containing conformationally restricted dehydrophenylalanine residue to
form ordered nanotubes. Adv Mater 19:858–861