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Keywords:

  • neurohypophyseal hormones;
  • disulfide bridge;
  • chiroptical spectroscopy;
  • circular dichroism;
  • Raman optical activity;
  • vibrational circular dichroism;
  • oxytocin;
  • vasopressin;
  • analogs;
  • conformation

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.