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Chemical Compound Review

SureCN59841     2-amino-2-phenyl-propanoic acid

Synonyms: CHEMBL203931, AG-F-98457, AG-G-70338, NSC-16591, CHEBI:440149, ...
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High impact information on NSC16591

  • Recently, we have synthesized two highly potent OT antagonists, [1-penicillamine, 4-threonine]OT ([Pen1, Thr4]OT) and [1-penicillamine, 2-phenylalanine, 4-threonine]OT ([Pen1, Phe2, Thr4]OT) [1].
  • Substituting 2-phenylalanine in [1-deaminopenicillamine]oxytocin also enhances antagonistic activities in all uterine assays, but [1-deaminopenicillamine, 2-phenylalanine]oxytocin retains agonistic activity on milk ejection assays [2].
  • In addition, APOBEC1 has a unique motif containing 2 phenylalanine residues and an insert of 4 amino acid residues across the active site motif [3].
  • This effect was mimicked by an AVP agonist (2-phenylalanine, 8-ornithine oxytocin) [4].
  • [1-Penicillamine, 2-phenylalanine, 4-threonine]-oxytocin has a weak antipressor activity and at high doses, consistently caused a weak and transient fall in blood pressure in the rat [5].

Anatomical context of NSC16591


  1. Antioxytocic and antiprostaglandin-releasing effects of oxytocin antagonists in pregnant rats and pregnant human myometrial strips. Chan, W.Y., Powell, A.M., Hruby, V.J. Endocrinology (1982) [Pubmed]
  2. The design of effective in vivo antagonists of rat uterus and milk ejection responses to oxytocin. Sawyer, W.H., Haldar, J., Gazis, D., Seto, J., Bankowski, K., Lowbridge, J., Turan, A., Manning, M. Endocrinology (1980) [Pubmed]
  3. An overview of cytidine deaminases. Navaratnam, N., Sarwar, R. Int. J. Hematol. (2006) [Pubmed]
  4. Effects of chronic icv infusion of vasopressin on sleep-waking cycle of rats. Arnauld, E., Bibene, V., Meynard, J., Rodriguez, F., Vincent, J.D. Am. J. Physiol. (1989) [Pubmed]
  5. Synthesis, pharmacological, conformational, and dynamic studies of the potent hormone antagonists [1-penicillamine, 4-threonine]-oxytocin and [1-penicillamine, 2-phenylalanine, 4-threonine]-oxytocin. Conformational and dynamic considerations in the design of antagonists. Hruby, V.J., Mosberg, H.I., Hadley, M.E., Chan, W.Y., Powell, A.M. Int. J. Pept. Protein Res. (1980) [Pubmed]
  6. The effects of 2-phenylalanine 8-lysine vasopressin (octapressin) on blood vessels in the rat tail. Frost, B.R., Gerke, D.C., Frewin, D.B. The Australian journal of experimental biology and medical science. (1976) [Pubmed]
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