ADDA (amino acid)

ADDA ((all-S,all-E)-3-amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid) is a non-proteinogenic amino acid found in toxins made by cyanobacteria. Toxins which include this amino acid include microcystins[1] and nodularins.

ADDA
Chemical structure of ADDA
Names
Preferred IUPAC name
(2S,3S,4E,6E,8S,9S)-3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid
Other names
(all-S,all-E)-3-Amino-9-methoxy-2,6,8-trimethyl-10-phenyldeca-4,6-dienoic acid
Identifiers
3D model (JSmol)
ChemSpider
  • InChI=1S/C20H29NO3/c1-14(10-11-18(21)16(3)20(22)23)12-15(2)19(24-4)13-17-8-6-5-7-9-17/h5-12,15-16,18-19H,13,21H2,1-4H3,(H,22,23)/b11-10+,14-12+/t15-,16-,18-,19-/m0/s1
    Key: HJVCHYDYCYBBQX-HLTLHRPFSA-N
  • InChI=1/C20H29NO3/c1-14(10-11-18(21)16(3)20(22)23)12-15(2)19(24-4)13-17-8-6-5-7-9-17/h5-12,15-16,18-19H,13,21H2,1-4H3,(H,22,23)/b11-10+,14-12+/t15-,16-,18-,19-/m0/s1
    Key: HJVCHYDYCYBBQX-HLTLHRPFBY
  • OC([C@@H](C)[C@@H](N)/C=C/C(C)=C/[C@H](C)[C@@H](OC)CC1=CC=CC=C1)=O
Properties
C20H29NO3
Molar mass 331.456 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Along with leucine and arginine, it is found in microcystin-LR, an extremely toxic compound produced by cyanobacteria. In order to treat a water supply contaminated with microcystin-LR, chlorination can be used to oxidize the double bonds of ADDA in order to initiate the chemical breakdown of this compound.[2]

References
  1. Rudolph-Böhner, Sabine; Mierke, Dale F.; Moroder, Luis (1994). "Molecular structure of the cyanobacterial tumor-promoting microcystins". FEBS Letters. 349 (3): 319–323. doi:10.1016/0014-5793(94)00680-6. PMID 8050589. S2CID 23312111.
  2. "ADDA". American Chemical Society. Retrieved 5 February 2023.
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