Conformational Analysis of a 20‐Membered Cyclic Peptide Disulfide from Conus virgo with a WPW Segment: Evidence for an Aromatic–Proline Sandwich
作者： Rajesh Sonti , K. N. Shashanka Rao , Sudarshan Chidanand , Konkallu Hanumae Gowd , Srinivasarao Raghothama
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摘要: A novel peptide containing a single disulfide bond, CIWPWC (Vi804), has been isolated and characterised from the venom of marine cone snail, Conus virgo. precursor polypeptide sequence derived complementary DNA, corresponding to M-superfamily conotoxins, identified. The identity synthetic natural established. detailed analysis conformation in solution is reported for Vi804 analogue, (CIWPWC)-W-D ((D)W3-Vi804), order establish structure WPW motif, which occurs context 20-membered macrocyclic disulfide. exists exclusively cis W3P4 conformer water methanol, whereas (D)W3-Vi804 as trans conformer. NMR spectra revealed typeVI turn typeII analogue peptide, (D)W3-Vi804. extremely high-field chemical shifts proline ring protons, together with specific nuclear Overhauser effects, are used sandwiched between flanking Trp residues, emphasises stabilising role aromatic-proline interactions, mediated predominantly by dispersion forces.
sci-hub.se 参考文章(75)
L J Cruz, V de Santos, G C Zafaralla, C A Ramilo, R Zeikus, W R Gray, B M Olivera, Invertebrate vasopressin/oxytocin homologs. Characterization of peptides from Conus geographus and Conus straitus venoms. Journal of Biological Chemistry. ,vol. 262, pp. 15821- 15824 ,(1987) , 10.1016/S0021-9258(18)47661-2
H.Jane Dyson, Mark Rance, Richard A. Houghten, Richard A. Lerner, Peter E. Wright, Folding of immunogenic peptide fragments of proteins in water solution Journal of Molecular Biology. ,vol. 201, pp. 161- 200 ,(1988) , 10.1016/0022-2836(88)90446-9
E.James Milner-White, Lachlan H. Bell, Peter H. Maccallum, Pyrrolidine ring puckering in cis and trans-proline residues in proteins and polypeptides. Different puckers are favoured in certain situations. Journal of Molecular Biology. ,vol. 228, pp. 725- 734 ,(1992) , 10.1016/0022-2836(92)90859-I
D. Langs, G. Smith, J. Stezowski, R. Hughes, Structure of pressinoic acid: the cyclic moiety of vasopressin. Science. ,vol. 232, pp. 1240- 1242 ,(1986) , 10.1126/SCIENCE.3704648
N. SRINIVASAN, R. SOWDHAMINI, C. RAMAKRISHNAN, P. BALARAM, Conformations of disulfide bridges in proteins International Journal of Peptide and Protein Research. ,vol. 36, pp. 147- 155 ,(2009) , 10.1111/J.1399-3011.1990.TB00958.X
Elsie C. Jimenez, Baldomero M. Olivera, Divergent M- and O-superfamily peptides from venom of fish-hunting Conus parius Peptides. ,vol. 31, pp. 1678- 1683 ,(2010) , 10.1016/J.PEPTIDES.2010.05.020
Paul K. Pallaghy, Weilan He, Elsie C. Jimenez, Baldomero M. Olivera, Raymond S. Norton, Structures of the contryphan family of cyclic peptides. Role of electrostatic interactions in cis-trans isomerism Biochemistry. ,vol. 39, pp. 12845- 12852 ,(2000) , 10.1021/BI0010930
Chelsea R. Martinez, Brent L. Iverson, Rethinking the term “pi-stacking” Chemical Science. ,vol. 3, pp. 2191- 2201 ,(2012) , 10.1039/C2SC20045G
Gloria P. Corpuz, Richard B. Jacobsen, Elsie C. Jimenez, Maren Watkins, Craig Walker, Clark Colledge, James E. Garrett, Owen McDougal, Wenqin Li, William R. Gray, David R. Hillyard, Jean Rivier, J. Michael McIntosh, Lourdes J. Cruz, Baldomero M. Olivera, Definition of the M-conotoxin superfamily: characterization of novel peptides from molluscivorous Conus venoms. Biochemistry. ,vol. 44, pp. 8176- 8186 ,(2005) , 10.1021/BI047541B
Elsie C. Jimenéz, Baldomero M. Olivera, William R. Gray, Lourdes J. Cruz, Contryphan Is a D-Tryptophan-containingConusPeptide Journal of Biological Chemistry. ,vol. 271, pp. 28002- 28005 ,(1996) , 10.1074/JBC.271.45.28002