Electronic and vibrational optical activity of several peptides related to neurohypophyseal hormones: Disulfide group conformation

Authors

  • Markéta Pazderková,

    Corresponding author
    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Fleming sq. 2, 166 10 Prague 6, Czech Republic
    2. Charles University in Prague, Faculty of Mathematics and Physics, Ke Karlovu 5, 121 16 Prague 2, Czech Republic
    • Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Fleming sq. 2, 166 10 Prague 6, Czech Republic
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  • Lucie Bednárová,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Fleming sq. 2, 166 10 Prague 6, Czech Republic
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  • Helena Dlouhá,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Fleming sq. 2, 166 10 Prague 6, Czech Republic
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  • Martin Flegel,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Fleming sq. 2, 166 10 Prague 6, Czech Republic
    2. Charles University in Prague, 1st Faculty of Medicine, Institute of Medical Biochemistry, Albertov 4, 128 00 Prague 2, Czech Republic
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  • Michal Lebl,

    1. Spyder Institut Praha s. r. o., Nad Safinou II c. 365, Vestec, 252 42 Jesenice u Prahy, Czech Republic
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  • Jan Hlaváček,

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Fleming sq. 2, 166 10 Prague 6, Czech Republic
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  • Vladimír Setnička,

    1. Institute of Chemical Technology Prague, Department of Physics, Technická 190, 166 28 Prague 6, Czech Republic
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  • Marie Urbanová,

    1. Institute of Chemical Technology Prague, Department of Physics, Technická 190, 166 28 Prague 6, Czech Republic
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  • Sixtus Hynie,

    1. Charles University in Prague, 1st Faculty of Medicine, Institute of Medical Biochemistry, Albertov 4, 128 00 Prague 2, Czech Republic
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  • Věra Klenerová,

    1. Charles University in Prague, 1st Faculty of Medicine, Institute of Medical Biochemistry, Albertov 4, 128 00 Prague 2, Czech Republic
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  • Vladimír Baumruk,

    1. Charles University in Prague, Faculty of Mathematics and Physics, Ke Karlovu 5, 121 16 Prague 2, Czech Republic
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  • Petr Maloň

    1. Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Fleming sq. 2, 166 10 Prague 6, Czech Republic
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  • This article was originally published online as an accepted preprint. The “Published Online” date corresponds to the preprint version. You can request a copy of the preprint by emailing the Biopolymers editorial office at biopolymers@wiley.com

Abstract

Electronic and vibrational optical activity of the set of neurohypophyseal hormones and their analogs was investigated to clarify the S[BOND]S bond solution conformation. The selected compounds include oxytocin (I), lysine vasopressin (II), arginine vasopressin (III), and their analogs (IV–IX), differing widely in their pharmacological properties. We have extended the already known electronic circular dichroism data by new information provided by vibrational circular dichroism (VCD) and Raman optical activity (ROA). The use of VCD brought additional details on three-dimensional structure of the chain reversal in the ring moiety and on its left handedness. Furthermore, Raman scattering and ROA allowed us to deduce the sense of the disulfide bond torsion. © 2012 Wiley Periodicals, Inc. Biopolymers 97:923–932, 2012.

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