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Tetrahydropyridine

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===Brettanomyces===
In ''Brettanomyces'', ATHP and ETHP are produced by metabolizing the amino acids L-Lysine and DL-Lysineornithine, along with ethanol and a glucose or fructose molecule<ref name="Snowdon"></ref>. As with other amino acids, lysine is taken up by ''Saccharomyces'' during fermentation, and then released after fermentation. Levels of lysine fluctuate slightly through fermentation, but are generally high throughout a beer's lifetime <ref>[http://link.springer.com/article/10.1385/CBB:46:1:43 The α-aminoadipate pathway for lysine biosynthesis in fungi. Hengyu Xu, Babak Andi, Jinghua Qian, Ann H. West , Paul F. Cook. Sept 2006.]</ref><ref>[http://pubs.acs.org/doi/abs/10.1021/bi9829940 Lysine Biosynthesis in Saccharomyces cerevisiae:  Mechanism of α-Aminoadipate Reductase (Lys2) Involves Posttranslational Phosphopantetheinylation by Lys5. David E. Ehmann , Amy M. Gehring , and Christopher T. Walsh. 1999.]</ref><ref>[http://onlinelibrary.wiley.com/doi/10.1002/j.2050-0416.2007.tb00249.x/abstract Elucidation of the Role of Nitrogenous Wort Components in Yeast Fermentation. C. Lekkas, G.G. Stewart, A.E. Hill, B. Taidi and J. Hodgson. May 2012.]</ref><ref>[http://www.sciencedirect.com/science/article/pii/S0308814699000710 Proteins and amino acids in beers, their contents and relationships with other analytical data. S. Gorinstein, M. Zemsera, F. Vargas-Albores, J-L. Ochoa, O. Paredes-Lopez, Ch. Scheler, J. Salnikow, O. Martin-Belloso, S. Trakhtenberg. 1999.]</ref>.
Oxygen has a stimulatory effect in it's production, but this is probably because ''Brett'' has a higher biomass formation under aerobic conditions <ref>[http://www.brettanomycesproject.com/dissertation/introduction/ Yakobson, Chad. The Brettanomyces Project; Introduction. Retrieved 3/10/2015.]</ref><ref>[http://pubs.acs.org/doi/abs/10.1021/jf071243e The Role of Lysine Amino Nitrogen in the Biosynthesis of Mousy Off-Flavor Compounds by Dekkera anomala. Paul R. Grbin, Markus Herderich, Andrew Markides, Terry H. Lee, and Paul A. Henschke. J. Agric. Food Chem., 2007.]</ref><ref name="Oelofse">[http://scholar.sun.ac.za/handle/10019.1/8437 Significance of Brettanomyces and Dekkera during Winemaking: A Synoptic Review. A. Oelofse, I.S. Pretorius, and M. du Toit. 2008.]</ref>. Therefore, limiting oxygen exposure during kegging/force carbonating is recommended for helping to reduce THP production. The level of THP production varies widely between species and strains of ''Brett'', with some strains not producing it at all and some producing very high amounts above taste threshold. Additionally, THP production appears to require glucose or fructose, which explains why THP may be seen more often in stuck wine fermentations rather than wine that has finished fermenting. ATHP production by ''Brett'' was observed in wine with glucose or fructose added, along with synthetic growth media, suggesting that the type of growth substrate does not effect production <ref>[http://www.ncbi.nlm.nih.gov/pubmed/18194246 Growth and volatile compound production by Brettanomyces/Dekkera bruxellensis in red wine. Romano A, Perello MC, de Revel G, Lonvaud-Funel A. J Appl Microbiol. 2008 Jun.]</ref>.
As ''Brett'' continues through it's growth cycle, ATHP is produced as a secondary metabolite <ref name="Snowdon"></ref>. ATHP is further metabolized into 2-ethyltetrahydropyridine (ETHP/ETPY) by ''Brettanomyces'', although not much is known about this metabolic process <ref>[http://ucce.ucdavis.edu/files/repositoryfiles/Joseph_5_Aromatic_Diverswity_of_Brettanomyces-82350.ppt Joseph, C.M. Lucy. ''Aromatic Diversity of Brettanomyces''. U.C. Davis. Retrieved 3/10/2015.]</ref>. ETHP has a significantly higher taste threshold, and is often not detected in contaminated wine <ref name="Oelofse"></ref>.
The presence of the "mousy off-flavor" caused by THP appears to be temporary in beer. Although not much is known about the degradation or metabolic break down of ATHP/ETHP, it tends to age out of beer after 2-6 months. Another unknown is why ''Brett'' produces THP shortly after kegging and force carbonating a beer that has reached final gravity. Pitching fresh ''Saccharomyces'' for bottle conditioning a beer with ''Brett'' in it has reportedly reduced THP production, perhaps through the quicker metabolism of both the oxygen and sugar that is introduced during packaging time.
===LAB===
Heterofermentative [[Lactobacillus]] spp., particularly ''L. hilgardii'' and ''L. brevis'', can also produce high levels of ATHP , ETHP, and ETHP APY from Lysine L-lysine/L-ornithine and ethanol <ref name="Costello">[http://pubs.acs.org/doi/abs/10.1021/jf020341r Mousy Off-Flavor of Wine:  Precursors and Biosynthesis of the Causative N-Heterocycles 2-Ethyltetrahydropyridine, 2-Acetyltetrahydropyridine, and 2-Acetyl-1-pyrroline by Lactobacillus hilgardii DSM 20176. Peter J. Costello and Paul A. Henschke. 2002.]</ref><ref>[http://www.ajevonline.org/content/37/2/127.abstract Formation of Substituted Tetrahydropyridines by Species of Brettanomyces and Lactobacillus Isolated from Mousy Wines. Tamila Heresztyn. 1986.]</ref><ref>[http://onlinelibrary.wiley.com/doi/10.1111/j.1755-0238.2001.tb00205.x/abstract Ability of lactic acid bacteria to produce N-heterocycles causing mousy off-flavour in wine. PETER J. COSTELLO1, TERRY H. LEE1, and PAULA. HENSCHKE. 2008.]</ref><ref>Sparrows, Jeff. ''Wild Brews''. Brewers Publications. 2005. Pg. 112.</ref><ref>[https://books.google.com/books?id=tFjsAuo5WocC&pg=PA348&lpg=PA348&dq=lactobacillus+Tetrahydropyridine&source=bl&ots=QUVyoFtIwK&sig=h1cdjB0r1pIRX2Bms8wVA0UiLk4&hl=en&sa=X&ei=4DX_VPz5CsH6oQSAzoGgBA&ved=0CEwQ6AEwCQ#v=onepage&q=lactobacillus%20Tetrahydropyridine&f=false Lahtinen, Ouwehand, Salminen, von Wright. Lactic Acid Bacteria: Microbiological and Functional Aspects, Fourth Edition. Pg 348.]</ref><ref>[http://ajevonline.org/content/37/2/127.short Heresztyn, Tamila. Formation of Substituted Tetrahydropyridines by Species of Brettanomyces and Lactobacillus Isolated from Mousy Wines.]</ref>. Most species of [[Pediococcus]] do not create THP, although a few species do. In particular, these include ''P. pentosaceus'' <ref>[http://www.uniprot.org/uniprot/Q03HT0 UniProt article. Retrieved 3/10/2015.]</ref><ref>[http://www.uniprot.org/uniprot/U5ZF76 UniProt article. Retrieved 3/10/2015.]</ref>, and ''P. clausenii'' <ref>[http://www.uniprot.org/uniprot/G8PEU4 UniProt article. Retrieved 3/10/2015.]</ref> (note that commercial cultures of [[Pediococcus]] are normally ''P. damnosus''). ''Oenococcus oeni'' and ''Leuconostoc mesenteroides'' have also been associated with creating THP . Since only heterofermentative species produce significant amounts of THP, it is thought that it's production is linked to the heterolactic pathway, and thus the metabolism of sugars in LAB <ref name="Costello"></ref>. ===AAB===Although research is limited, acetic acid bacteria have been shown to occasionally produce forms of THP <ref name="Snowdon"></ref>.
==Thresholds==

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