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the (116), methionine (98), and (80), acid (51), amino (43), coa (29), doi (26), edit (26), with (24), pmid (23), acids (21), other (21), #cysteine (21), for (21), from (20), homocysteine (17), #biosynthesis (14), can (14), pathway (14), chemical (13), cystathionine (13), which (13), this (12), also (12), that (12), citation (12), needed (12), articles (11), proteins (11), protein (11), codon (11), are (11), 1016 (10), used (10), group (10), multiple (9), encoded (9), biochemical (9), via (9), page (8), s2cid (8), journal (8), toggle (7), code (7), wikipedia (7), may (7), using (7), names (7), sulfur (7), proteinogenic (7), against (7), food (7), pathways (7), not (7), adenosylmethionine (7), homoserine (7), where (7), containing (6), data (6), essential (6), metabolism (6), see (6), methyl (6), semialdehyde (6), restriction (6), 2018 (6), 2011 (6), role (6), enzymes (6), hydrogen (6), methanethiol (6), enzyme (6), synthase (6), rsam (6), main (6), bacteria (6), aug (6), was (5), cs1 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tivating group is then replaced with cysteine methanethiol or hydrogen sulfide a replacement reaction is technically a γ elimination followed by a variant of a michael addition all the enzymes involved are homologues and members of the cys met metabolism plp dependent enzyme family which is a subset of the plp dependent fold type i clade they utilise the cofactor plp pyridoxal phosphate which functions by stabilising carbanion intermediates 9 if it reacts with cysteine it produces cystathionine which is cleaved to yield homocysteine the enzymes involved are cystathionine γ synthase encoded by metb in bacteria and cystathionine β lyase metc cystathionine is bound differently in the two enzymes allowing β or γ reactions to occur 9 if it reacts with free hydrogen sulfide it produces homocysteine this is catalysed by o acetylhomoserine aminocarboxypropyltransferase formerly known as o acetylhomoserine thiol lyase it is encoded by either mety or metz in bacteria 9 if it reacts with methanethiol it produces methionine directly methanethiol is a byproduct of catabolic pathway of certain compounds therefore this route is more uncommon 9 if homocysteine is produced the thiol group is methylated yielding methionine two methionine synthases are known one is cobalamin vitamin b 12 dependent and one is independent 9 the pathway using cysteine is called the transsulfuration pathway while the pathway using hydrogen sulfide or methanethiol is called direct sulfurylation pathway cysteine is similarly produced namely it can be made from an activated glycine and either from homocysteine reverse transsulfurylation route or from hydrogen sulfide direct sulfurylation route the activated serine is generally o acetylserine via cysk or cysm in e coli but in aeropyrum pernix and some other archaea o phosphoserine is used 16 cysk and cysm are homologues but belong to the plp fold type iii clade citation needed transsulfurylation pathway edit main article transsulfuration pathway enzymes involved in the e coli transsulfurylation route of methionine biosynthesis 17 aspartokinase aspartate semialdehyde dehydrogenase homoserine dehydrogenase homoserine o transsuccinylase cystathionine γ synthase cystathionine β lyase methionine synthase in mammals this step is performed by homocysteine methyltransferase or betaine homocysteine s methyltransferase other biochemical pathways edit fates of methionine although mammals cannot synthesize methionine they can still use it in a variety of biochemical pathways catabolism edit methionine is converted to s adenosylmethionine rsam by 1 methionine adenosyltransferase citation needed rsam serves as a methyl donor in many 2 methyltransferase reactions and is converted to s adenosylhomocysteine sah citation needed 3 adenosylhomocysteinase cysteine regeneration edit methionine can be regenerated from homocysteine via 4 methionine synthase in a reaction that requires vitamin b 12 as a cofactor citation needed homocysteine can also be remethylated using glycine betaine n n n trimethylglycine tmg to methionine via the enzyme betaine homocysteine methyltransferase e c 2 1 1 5 bhmt bhmt makes up to 1 5 of all the soluble protein of the liver and recent evidence suggests that it may have a greater influence on methionine and homocysteine homeostasis than methionine synthase citation needed reverse transulfurylation pathway conversion to cysteine edit homocysteine can be converted to cysteine 5 cystathionine β synthase an enzyme which requires pyridoxal phosphate the active form of vitamin b6 combines homocysteine and serine to produce cystathionine instead of degrading cystathionine via cystathionine β lyase as in the biosynthetic pathway cystathionine is broken down to cysteine and α ketobutyrate via 6 cystathionine γ lyase citation needed 7 the enzyme α ketoacid dehydrogenase converts α ketobutyrate to propionyl coa which is metabolized to succinyl coa in a three step process see propionyl coa for pathway citation needed metabolic diseases edit the degradation of methionine is impaired in the following metabolic diseases citation needed combined malonic and methylmalonic aciduria cmamma homocystinuria methylmalonic acidemia propionic acidemia chemical synthesis edit the industrial synthesis combines acrolein methanethiol and cyanide which affords the hydantoin 18 racemic methionine can also be synthesized from diethyl sodium phthalimidomalonate by alkylation with chloroethylmethylsulfide clch 2 ch 2 sch 3 followed by hydrolysis and decarboxylation also see methanol 19 human nutrition edit there is inconclusive clinical evidence on methionine supplementation 20 dietary restriction of methionine can lead to bone related disorders 20 overconsumption of methionine the methyl group donor in dna methylation is related to cancer growth in a number of studies 21 22 requirements edit the food and nutrition board of the u s institute of medicine set recommended dietary allowances rdas for essential amino acids in 2002 for methionine combined with cysteine for adults 19 years and older 19 mg kg body weight day 23 this translates to about 1 33 grams per day for a 70 kilogram individual citation needed dietary sources edit food sources of methionine citation needed food g 100 g egg white dried powder glucose reduced 3 204 sesame seeds flour low fat 1 656 brazil nuts 1 124 cheese parmesan shredded 1 114 hemp seed hulled 0 933 soy protein concentrate 0 814 chicken broilers or fryers roasted 0 801 fish tuna light canned in water drained solids 0 755 beef cured dried 0 749 bacon 0 593 chia seeds 0 588 beef ground 95 lean meat 5 fat raw 0 565 pork ground 96 lean 4 fat raw 0 564 soybeans 0 547 wheat germ 0 456 egg whole cooked hard boiled 0 392 oat 0 312 peanuts 0 309 chickpea 0 253 corn yellow 0 197 almonds 0 151 beans pinto cooked 0 117 lentils cooked 0 077 rice brown medium grain cooked 0 052 high levels of methionine can be found in eggs meat and fish sesame seeds brazil nuts and some other plant seeds and cereal grains most fruits and vegetables contain very little most legumes though protein dense are low in methionine proteins without adequate methionine are not considered to be complete proteins 24 for that reason racemic methionine is sometimes added as an ingredient to pet foods 25 health edit loss of methionine has been linked to senile greying of hair its lack leads to a buildup of hydrogen peroxide in hair follicles a reduction in tyrosinase effectiveness and a gradual loss of hair color 26 methionine raises the intracellular concentration of glutathione thereby promoting antioxidant mediated cell defense and redox regulation it also protects cells against dopamine induced nigral cell loss by binding oxidative metabolites 27 methionine is an intermediate in the biosynthesis of cysteine carnitine taurine lecithin phosphatidylcholine and other phospholipids improper conversion of methionine can lead to atherosclerosis 28 due to accumulation of homocysteine other uses edit dl methionine is sometimes given as a supplement to dogs it helps reduce the chances of kidney stones in dogs methionine is also known to increase the urinary excretion of quinidine by acidifying the urine aminoglycoside antibiotics used to treat urinary tract infections work best in alkaline conditions and urinary acidification from using methionine can reduce its effectiveness if a dog is on a diet that acidifies the urine methionine should not be used 29 methionine is allowed as a supplement to organic poultry feed under the us certified organic program 30 methionine can be used as a nontoxic pesticide option against giant swallowtail caterpillars which are a serious pest to orange crops 31 restricting methionine intake edit more and more studies show that restricting methionine intake can increase the lifespan of some animals 32 33 in 2005 a study showed that restricting methionine intake without energy restriction in rodents increases their lifespan 34 see also edit 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