Vargulin

Vargulin
Names
IUPAC name
2-[3-[2-[(2S)-butan-2-yl]-6-(1H-indol-3-yl)-3-oxo-7H-imidazo[2, 1-c]pyrazin-8-yl]propyl]guanidine
Other names
  • Cypridina luciferin
  • Cypridinid luciferin
  • Vargula luciferin
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C22H27N7O/c1-3-13(2)19-21(30)29-12-18(15-11-26-16-8-5-4-7-14(15)16)27-17(20(29)28-19)9-6-10-25-22(23)24/h4-5,7-8,11-13,26-27H,3,6,9-10H2,1-2H3,(H4,23,24,25) checkY
    Key: ZWPWSXGBDMGKKS-UHFFFAOYSA-N checkY
  • InChI=1S/C22H27N7O/c1-3-13(2)19-21(30)29-12-18(15-11-26-16-8-5-4-7-14(15)16)27-17(20(29)28-19)9-6-10-25-22(23)24/h4-5,7-8,11-13,26-27H,3,6,9-10H2,1-2H3,(H4,23,24,25)/t13-/m0/s1
    Key: ZWPWSXGBDMGKKS-UHFFFAOYAG
  • O=C\3N4\C=C(\c2c1ccccc1[nH]c2)N/C(=C4/N=C/3[C@@H](C)CC)CCC/N=C(\N)N
Properties
C22H27N7O
Molar mass 405.506 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vargulin,[1] also called Cypridinid luciferin,[2] Cypridina luciferin, or Vargula luciferin, is the luciferin found in the ostracod Cypridina hilgendorfii, also named Vargula hilgendorfii.[3] These bottom dwelling ostracods emit a light stream into water when disturbed presumably to deter predation. Vargulin is also used by the midshipman fish, Porichthys.

History

A partial extraction procedure was developed in 1935 which involved reacting the compound with benzoyl chloride to allow it to be separated from the water-soluble components.[4] The compound was first isolated and purified to crystals by Osamu Shimomura.[5] The structure of the compound was confirmed some years later.[6] Feeding experiments suggest that the compound is synthesized in the animal from three amino-acids: tryptophan, isoleucine, and arginine.[7]

Biochemistry

Vargulin is oxidized by cypridina-luciferin 2-monooxygenase,[8][9][10] a 62 kDa enzyme, to produce blue light at 462 nm (max emission, detected with a 425 to 525 nm filter).

2D representation of the chemical structure of vargulin .
vargulin
 
O2
CO2
Rightward reaction arrow with minor substrate(s) from top left and minor product(s) to top right
 
 
 
2D representation of the chemical structure of Q27102268.
oxidized vargulin
+ hν
 


The vargulin does not cross react with luciferases using coelenterazine or Firefly luciferin.

Uses

Vargulin (with the associated luciferase) has applications in biotechnology:

Although less stable, the Cypridina system is useful because can be used in multiplex assays with other (red-emitting) luciferin assays.

References

  1. ^ Campbell AK, Herring PJ (1990). "Imidazolopyrazine bioluminescence in copepods and other marine organisms". Marine Biology. 104 (2). Springer Science and Business Media LLC: 219–225. Bibcode:1990MarBi.104..219C. doi:10.1007/bf01313261. ISSN 0025-3162. S2CID 84250053.
  2. ^ Morin JG (2011). "Based on a review of the data, use of the term 'cypridinid' solves the Cypridina/Vargula dilemma for naming the constituents of the luminescent system of ostracods in the family Cypridinidae". Luminescence. 26 (1). Wiley: 1–4. doi:10.1002/bio.1282. ISSN 1522-7235. PMID 19862683.
  3. ^ Shimomura, O. (2006). Bioluminescence: Chemical Principles and Methods. World Scientific Publishing. ISBN 978-981-256-801-4.
  4. ^ Anderson, RS (1935). "Studies on Bioluminescence : II. the Partial Purification of Cypridina Luciferin". The Journal of General Physiology. 19 (2): 301–5. doi:10.1085/jgp.19.2.301. PMC 2141430. PMID 19872927.
  5. ^ Shimomura, O, Goto, T, Hirata, Y (1957). "Crystalline Cypridina Luciferin". Bulletin of the Chemical Society of Japan. 30 (8): 929–933. doi:10.1246/bcsj.30.929. hdl:10069/20882.
  6. ^ Kishi Y, Goto, T, Hirata Y, Shiromura O, Johnson FH (1966). "Cypridina bioluminescence. I. Structure of Cypridina luciferin". Tetrahedron Lett. 7 (29): 3427–3436. doi:10.1016/S0040-4039(01)82806-9.
  7. ^ Oba, Y, Kato, S, Ojika, M, Inouye, S (2002). "Biosynthesis of luciferin in the sea firefly, Cypridina hilgendorfii: L-tryptophan is a component in Cypridina luciferin". Tetrahedron Letters. 43 (12): 2389–2392. doi:10.1016/S0040-4039(02)00257-5.
  8. ^ Thompson EM, Nagata S, Tsuji FI (1989). "Cloning and expression of cDNA for the luciferase from the marine ostracod Vargula hilgendorfii". Proceedings of the National Academy of Sciences. 86 (17): 6567–71. Bibcode:1989PNAS...86.6567T. doi:10.1073/pnas.86.17.6567. PMC 297885. PMID 2771943.
  9. ^ Karpetsky TP, White EH (1973). "The synthesis of Cypridina etioluciferamine and the proof of the structure of Cypridina luciferin". Tetrahedron. 29 (23): 3761–3773. doi:10.1016/0040-4020(73)80193-0.
  10. ^ Tsuji FI, Lynch RV III, Stevens CL (1974). "Some properties of luciferase from the bioluminescent crustacean, Cypridina hilgendorfii". Biochemistry. 13 (25): 5204–5209. doi:10.1021/bi00722a024. PMID 4433517.
  11. ^ "Luciferase Reporters". thermofisher.com.
  • Wikimedia Commons logo Media related to Vargulin at Wikimedia Commons

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