| Revision as of 09:25, 9 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chem← Previous edit |
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{{chembox |
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{{chembox |
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| verifiedrevid = 443839308 |
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| Watchedfields = changed |
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| ImageFile = glycocyamine.png |
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| verifiedrevid = 443840383 |
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| ImageSize = 190px |
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| ImageFile = glycocyamine.png |
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| ImageName = Skeletal formula |
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| ImageFile_Ref = {{chemboximage|correct|??}} |
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| ImageFile1 = Glycocyamine-3D-balls.png |
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| ImageSize1 = 210px |
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| ImageSize = 160 |
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| ImageName = Skeletal formula of a glycocyamine minor tautomer |
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| ImageName1 = Ball-and-stick model |
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| ImageFile1 = Glycocyamine-3D-balls.png |
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| IUPACName = 2-Guanidinoacetic acid |
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| ImageFile1_Ref = {{chemboximage|correct|??}} |
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| OtherNames = Guanidinoacetic acid; ''N''-Amidinoglycine; ''N''-Guanylglycine |
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| ImageSize1 = 160 |
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| ImageName1 = Ball and stick model of a glycocyamine minor tautomer |
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| ImageFile2 = Glycocyamine-3D-spacefill.png |
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| ImageFile2_Ref = {{chemboximage|correct|??}} |
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| ImageSize2 = 160 |
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| ImageName2 = Spacefill model of a glycocyamine minor tautomer |
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|IUPACName=''N''-Carbamimidoylglycine |
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|SystematicName=2-(Diaminomethylideneamino)acetic acid |
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| OtherNames = 2-Guanidinoacetic acid{{citation needed|date=July 2012}} |
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|Section1={{Chembox Identifiers |
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|Section1={{Chembox Identifiers |
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| CASNo=352-97-6 |
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| CASNo = 352-97-6 |
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| CASNo_Ref = {{cascite|correct|??}} |
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| PubChem=763 |
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| PubChem = 763 |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| ChemSpiderID = 743 |
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| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
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| UNII = GO52O1A04E |
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| UNII = GO52O1A04E |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| SMILES=C(C(=O)O)N=C(N)N |
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| EINECS = 206-529-5 |
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| MeSHName=Glycocyamine |
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| DrugBank_Ref = {{drugbankcite|changed|drugbank}} |
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}} |
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| DrugBank = DB02751 |
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| KEGG = C00581 |
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| KEGG_Ref = {{keggcite|changed|kegg}} |
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| MeSHName = glycocyamine |
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| ChEBI = 16344 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEMBL = 281593 |
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| ChEMBL_Ref = {{ebicite|changed|EBI}} |
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| Beilstein = 1759179 |
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| 3DMet = B00139 |
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| SMILES = NC(=N)NCC(O)=O |
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| StdInChI = 1S/C3H7N3O2/c4-3(5)6-1-2(7)8/h1H2,(H,7,8)(H4,4,5,6) |
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| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
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| StdInChIKey = BPMFZUMJYQTVII-UHFFFAOYSA-N |
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| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
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}} |
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|Section2={{Chembox Properties |
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|Section2={{Chembox Properties |
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| C=3 | H=7 | N=3 | O=2 |
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| Formula=C<sub>3</sub>H<sub>7</sub>N<sub>3</sub>O<sub>2</sub> |
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| Appearance = White crystals |
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| MolarMass=117.11 g/mol |
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| Odor = Odourless |
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| Appearance= |
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| MeltingPtC = 300 |
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| Density= |
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| LogP = −1.11 |
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| MeltingPt= |
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| pKa = 3.414 |
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| BoilingPt= |
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| pKb = 10.583 |
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| Solubility= |
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}} |
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}} |
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|Section3={{Chembox Hazards |
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|Section3={{Chembox Hazards |
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| GHSPictograms = {{gHS exclamation mark}} |
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| MainHazards= |
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| GHSSignalWord = '''WARNING''' |
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| FlashPt= |
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| HPhrases = {{h-phrases|315|319|335}} |
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| Autoignition= |
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| PPhrases = {{p-phrases|261|305+351+338}} |
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}} |
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}} |
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|Section4={{Chembox Related |
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| OtherFunction_label = alkanoic acids |
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| OtherFunction = {{unbulleted list|]|]|]|]|]|]}} |
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| OtherCompounds = ] |
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'''Glycocyamine''' (or '''guanidinoacetate''') is a metabolite of ] in which the ] has been converted into a ]. |
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'''Glycocyamine''' (or '''guanidinoacetate''') is a metabolite of ] in which the ] has been converted into a ] by guanylation (transfer of a guanidine group from ]). In vertebrate organism it is then transformed into ] by ]. |
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Glycocyamine is a direct precursor of ] and is used as a supplement. However the metabolism of creatine from glycocyamine in the liver causes a depletion of ]s. This causes ] levels to rise, which has been shown to produce cardiovascular and skeletal problems. |
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Glycocyamine is used as a supplement and as a ] in ]. However, the metabolism of creatine from glycocyamine in the liver causes a depletion of ]s. This causes ] levels to rise, which has been shown to produce cardiovascular and skeletal problems.{{Citation needed|date=March 2018}} Glycocyamine plays a role in the metabolism of the amino acids ], ], and ]. |
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== Uses == |
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== Production == |
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A series of studies showed that a combination of ] and glycocyamine improves the symptoms of patients with chronic illness, including heart disease, without ]. Betaine can provide a ] group to glycocyamine, via ], for the formation of creatine. <ref> Borsook H, Borsook ME. The biochemical basis of betaine-glycocyamine therapy. Ann West Med Surg 1951;5:825–9. </ref> |
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In overal, such treatment led to less fatigue, greater strength and endurance, and an improved sense of well-being. The patients with cardiac decompensation (] or ]) <ref> Borsook ME, Borsook H. Treatment of cardiac decompensation with betaine and glycocyamine. Ann West Med Surg 1951;5:830–55. </ref> and congestive ] <ref> Van Zandt V, Borsook H. New biochemical approach to the treatment of congestive heart failure. Ann West Med Surg 1951;5:856–62.</ref> had improved cardiac function. |
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The patients gained weight (improved ] balance) and saw lessened symptoms of ] and ] and increased ], and those people suffering from ] experienced transient reduced ]. Also the studies shows the increase of glucose tolerance in both diabetic subjects and subjects without diabetes. <ref> {{cite journal |author= Stuart AS Craig |year=2004 |month=September |title= Betaine in human nutrition |journal= American Journal of Clinical Nutrition |volume=80 |issue=3 |pages=539–549 |url=http://www.ajcn.org/cgi/content/full/80/3/539 |accessdate=2010-02-10 |pmid= 15321791 }} </ref> |
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=== Biochemical synthesis === |
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== References == |
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Glycocyamine is formed in the mammalian organism primarily in the ] by transferring the ] of L-arginine by the enzyme ] (AGAT) to the amino acid glycine. From L-arginine, ] is thus produced, which is metabolized in the ] by carbamoylation to ]. |
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<references/> |
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] |
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==External links== |
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In a further step, glycocyamine is methylated to creatine with ] by the enzyme ] (GAMT). The creatine is released into the ]. |
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=== Chemical synthesis === |
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Guanidinoacetic acid was first prepared in 1861 by ]<ref>M. Strecker, Jahresber. Fortschr. Chem. Verw., (1861), 530, {{doi|10.1002/jlac.18611180303}}</ref> by reaction of ] with ] in aqueous solution: |
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Glycine can also be converted to glycocyamine with ''S''-methylisothiourea<ref>H.I. Wheeler, H.F. Merriam, J.Amer.Chem.Soc., '''29''' (1903), 478–492.</ref> or with ''O''-alkylisoureas<ref>Alzchem: (PDF; 844 kB), Ausgabe 1/2011.</ref> as a guanylation agent. |
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] |
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The recent patent literature describes the synthesis of glycocyamine by catalytic oxidation of ] to glycine and subsequent reaction with cyanamide in aqueous solution in high yield, analogous to the synthesis of ] starting from ] via ].<ref>{{Cite patent | country =US | number = 8227638| Typ = | title =Process for preparing creatine, creatine monohydrate and guanidinoacetic acid | A-Datum = | gdate = 2012-07-24| invent1 =F. Thalhammer, T. Gastner | assign1 =Alzchem Trostberg GmbH | DB = }}</ref> |
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] |
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This synthetic route suppresses the formation of toxic ] and other undesired by-products (such as ]). |
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== Properties == |
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Industrially produced guanidinoacetic acid is sold as a white (to yellowish) fine powder, which is granulated for improve handling, metering and uptake with starch into aggregates with a mean diameter of 200-400 microns.<ref>{{Cite patent | country =US | number =2010143703 | Typ = | title =Abrasion-resistant free-flowing glycocyamine-containing mouldings and methods for their production | A-Datum = | gdate = 2010-06-10| invent1 =S. Winkler et al. | assign1 = }}</ref> The granulate provides a long-term stability of glycocyamine. The shelf Life of guanidinoacetate in acidic aqueous solution is significantly higher than that of creatine, which cyclizes to ] under acid catalysis. |
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==Uses== |
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===As a supplement=== |
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A series of studies showed that a combination of ] and glycocyamine improves the symptoms of patients with chronic illness, including heart disease, without ]. Betaine can provide a ] group to glycocyamine, via ], for the formation of creatine.<ref> Borsook H, Borsook ME. The biochemical basis of betaine-glycocyamine therapy. Ann West Med Surg 1951;5:825–9.</ref> In overall, such treatment led to less fatigue, greater strength and endurance, and an improved sense of well-being. The patients with cardiac decompensation (] or ])<ref>Borsook ME, Borsook H. Treatment of cardiac decompensation with betaine and glycocyamine. Ann West Med Surg 1951;5:830–55.</ref> and congestive ]<ref> Van Zandt V, Borsook H. New biochemical approach to the treatment of congestive heart failure. Ann West Med Surg 1951;5:856–62.</ref> had improved cardiac function. The patients gained weight (improved ] balance) and saw lessened symptoms of ] and ] and increased ], and those people suffering from ] experienced transient reduced ]. Also the studies shows the increase of glucose tolerance in both diabetic subjects and subjects without diabetes.<ref> {{cite journal |author= Stuart AS Craig |date=September 2004 |title= Betaine in human nutrition |journal= American Journal of Clinical Nutrition |volume=80 |issue=3 |pages=539–549 |url=http://www.ajcn.org/cgi/content/full/80/3/539 |access-date=2010-02-10 |pmid= 15321791 |doi=10.1093/ajcn/80.3.539|doi-access=free }}</ref> |
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=== As a feed additive === |
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Guanidinoacetic acid is a nutritional ] approved by ] for chickens for fattening, weaned piglets and pigs for fattening.<ref>COMMISSION IMPLEMENTING REGULATION (EU) 2016/1768 of 4 October 2016 concerning the authorisation of guanidinoacetic acid as a feed additive for chickens for fattening, weaned piglets and pigs for fattening and repealing Commission Regulation (EC) No 904/2009</ref> It is supposed to lead with a "vegetarian diet" (meaning without feeding of animal protein) to higher feed conversion, higher weight gain and improved muscle increase already at a low dosage (600 g/to feed).<ref>{{Cite patent | country =EP | number =1758463 | Typ = | title =GUANIDINO ACETIC ACID USED AS AN ANIMAL FOOD ADDITIVE | A-Datum = | gdate =2007-12-26 | invent1 = T. Gastner, H.-P. Krimmer| assign1 =Degussa AG | DB = }}.</ref> |
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Possible benefits of glycocyamine supplementation can not yet be conclusively assessed, neither in other breeding, fattening and domestic animals nor for high-performance athletes, analogous to the glycocyamine metabolite creatine. The simultaneous intake of methyl providing substances such as ] appears advisable because of the risk of ] formation with glycocyamine alone.<ref>S.M. Ostojic et al., ''Co-administration of methyl donors along with guanidinoacetic acid reduces the incidence of hyperhomocysteinaemia compared with guanidinoacetic acid administration alone'', Br. J. Nutr. (2013), Jan 28:1-6 {{doi| 10.1017/S0007114512005879}}</ref> |
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==References== |
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{{reflist}} |
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==See also== |
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==See also== |
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* ] |
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{{Amino acid metabolism intermediates}} |
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{{amino acid metabolism intermediates}} |
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{{organic-compound-stub}} |
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