Mirabamide Explained

Mirabamides are sea sponge isolates that inhibit HIV-1 fusion.[1] Variants A to D are known from Siliquariaspongia mirabilis and E through H are derived from Stelletta clavosa.[2] Mirabamides have a macrocyclic region closed through an ester bond between the C-terminus and a -hydroxyl group, and terminated with a polyketide moiety or a more simple branched aliphatic acid.[3]

Mirabamide G is a fusion of several amino acids: 2,3 diamino butanoic acid, 3-hydroxyleucine, N-methylthreonine, 2,3-dihydroxy-2,6,8-trimethyldeca-(4Z,6E)-dienoic acid, 3-methoxy alanine, β-methoxytyrosine, 3,4-dimethylglutamine.[4]

References

attribution: Contains text from the CC/BY/4.0 licensed "Chemical Reactivity Properties, pKa Values, AGEs Inhibitor Abilities and Bioactivity Scores of the Mirabamides A–H Peptides of Marine Origin Studied by Means of Conceptual DFT" by Lazcano-Perez et al.

Notes and References

  1. 17963357. 2007. Plaza. A. Gustchina. E. Baker. HL. Kelly. M. Bewley. CA. Mirabamides A-D, depsipeptides from the sponge Siliquariaspongia mirabilis that inhibit HIV-1 fusion. 70. 11. 1753–60. 10.1021/np070306k. Journal of Natural Products.
  2. Lu . Zhenyu . Van Wagoner . Ryan M. . Harper . Mary Kay . Baker . Heather L. . Hooper . John N. A. . Bewley . Carole A. . Ireland . Chris M. . Mirabamides E−H, HIV-Inhibitory Depsipeptides from the Sponge Stelletta clavosa . Journal of Natural Products . 25 February 2011 . 74 . 2 . 185–193 . 10.1021/np100613p. 21280591 . 3072293 .
  3. Frau . Juan . Flores-Holguín . Norma . Glossman-Mitnik . Daniel . Chemical Reactivity Properties, pKa Values, AGEs Inhibitor Abilities and Bioactivity Scores of the Mirabamides A–H Peptides of Marine Origin Studied by Means of Conceptual DFT . Marine Drugs . 28 August 2018 . 16 . 9 . 302 . 10.3390/md16090302. 30154377 . 6163382 . free .
  4. Lazcano-Perez . Fernando . Roman-Gonzalez . Sergio A. . Sanchez-Puig . Nuria . Espinosa . Roberto Arreguin- . Bioactive Peptides from Marine Organisms: A Short Overview . Protein and Peptide Letters . 2012 . 19 . 7 . 700–707 . 10.2174/092986612800793208. 22489781 .