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D-Aminolevulinic acid



D-Aminolevulinic acid
Systematic (IUPAC) name
5-amino-4-oxo-pentanoic acid
Identifiers
CAS number 106-60-5
ATC code L01XD04
PubChem 137
DrugBank APRD00793
Chemical data
Formula C5H9NO3 
Mol. mass 131.13 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
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Therapeutic considerations
Pregnancy cat.

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Legal status
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D-Aminolevulinic acid (dALA or δ-ALA or 5-aminolevulinic acid) is the first compound in the porphyrin synthesis pathway, the pathway that leads to hemoglobin in mammals.

Additional recommended knowledge

In non-photosynthetic eukaryotes such as animals, insects, fungi, and protozoa as well as the α-proteobacteria group of bacteria it is produced by the enzyme ALA synthase, from glycine and succinyl CoA. This reaction is known as the Shemin pathway.

In plants, algae, bacteria (except for the α-proteobacteria group) and archaea it is produced from glutamic acid via glutamyl-tRNA and glutamate-1-semialdehyde. The enzymes involved in this pathway are glutamyl-tRNA synthetase, glutamyl-tRNA reductase and glutamate-1-semialdehyde aminotransferase. This pathway is known as the C5 or Beale pathway.[1][2]

Clinical significance

It elicits synthesis and accumulation of fluorescent porphyrins (protoporphyrin IX) in epithelia and neoplastic tissues, among them malignant gliomas. It is used to visualise tumorous tissue in neurosurgical procedures. Studies [3] have shown that the intraoperative use of this guiding method may reduce the tumour residual volume and prolong progression-free survival in patients suffering from this disease.

dALA is also a photosensitizer for photodynamic therapy.

References

  1. ^ Beale, Samuel I. (1990) Biosynthesis of the tetrapyrrole pigment precursor, d-aminolevulinic acid, from glutamate. Plant Physiology, 93(4), 1273-1279
  2. ^ Willows R.D. (2004) Chlorophylls In: Encylopaedia of Plant and Crop Science. pp 258-262, Ed: Robert M. Goodman. Marcel Dekker Inc, ISBN 0-8247-4268-0
  3. ^ Stummer W, Pichlmeier U, Meinel T, Wiestler OD, Zanella F, Reulen HJ (2006). "Fluorescence-guided surgery with 5-aminolevulinic acid for resection of malignant glioma: a randomised controlled multicentre phase III trial". Lancet Oncol. 7 (5): 392-401. doi:10.1016/S1470-2045(06)70665-9. PMID 16648043.

See also

 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "D-Aminolevulinic_acid". A list of authors is available in Wikipedia.
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