Editing Ephedrine (section)

===Biosynthetic===
[[File:Ephedrine biosynthesis.svg|class=skin-invert-image|thumb|400px|right|Proposed biosynthetic pathway of ephedrine from <small>L</small>-phenylalanine and pyruvic acid.<ref name="Hertweck">{{cite journal | vauthors = Hertweck C, Jarvis AP, Xiang L, Moore BS, Oldham NJ | title = A mechanism of benzoic acid biosynthesis in plants and bacteria that mirrors fatty acid beta-oxidation | journal = ChemBioChem | volume = 2 | issue = 10 | pages = 784–6 | date = October 2001 | pmid = 11948863 | doi = 10.1002/1439-7633(20011001)2:10<784::AID-CBIC784>3.0.CO;2-K | s2cid = 28159196 }}<!--|access-date = 2015-06-10--></ref><ref name="Grue-Sorensen 3714–3715">{{Cite journal |title= Biosynthesis of ephedrine |journal= Journal of the American Chemical Society |date= May 1, 1988 |issn= 0002-7863 |pages= 3714–3715 |volume= 110 |issue= 11 |doi= 10.1021/ja00219a086 | vauthors = Grue-Sorensen G, Spenser ID |bibcode= 1988JAChS.110.3714G }}</ref>]]

Ephedrine was long thought to come from modifying the amino acid <small>L</small>-phenylalanine.<ref name="sciencedirect.com">{{cite journal |title= Participation of C6-C1 unit in the biosynthesis of ephedrine in Ephedra |doi= 10.1016/0031-9422(73)80499-6 |volume=12 |issue=12 |journal= Phytochemistry |pages= 2877–2882 |year= 1973 | vauthors = Yamasaki K, Tamaki T, Uzawa S, Sankawa U, Shibata S |bibcode= 1973PChem..12.2877Y }}</ref> <small>L</small>-Phenylalanine would be decarboxylated and subsequently attacked with ω-aminoacetophenone. Methylation of this product would then produce ephedrine. This pathway has since been disproven.<ref name="sciencedirect.com"/> A new pathway proposed suggests that phenylalanine first forms [[cinnamoyl-CoA]] via the enzymes [[phenylalanine ammonia-lyase]] and acyl CoA ligase.<ref name="Hertweck"/> The cinnamoyl-CoA is then reacted with a hydratase to attach the alcohol functional group. The product is then reacted with a retro-aldolase, forming [[benzaldehyde]]. Benzaldehyde reacts with [[pyruvic acid]] to attach a 2-carbon unit. This product then undergoes transamination and methylation to form ephedrine and its stereoisomer, pseudoephedrine.<ref name="Grue-Sorensen 3714–3715"/>