Glycocyamine

• Guanidinoacetate
• Guanidinoacetic acid
• Glycocyamine
• N- Guanylglycine
• N- Amidinoglycin
• N-( aminoiminomethyl ) glycine

White to pale yellow, odorless, crystalline solid

Fixed

300 ° C.

Soluble in water (4 g · l -1)

Attention

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Guanidinoacetic ( guanidinoacetate, or English. Guanidinoacetic acid, GAA) is formed ( transfer of a guanidine group of arginine ) in the body of vertebrates from glycine by guanylation and converted by subsequent methylation to creatine. It is even no amino acid, but also plays a role in the metabolism of canonical amino acids serine, threonine and proline. GAA is used as a feed additive in poultry feed.

Representation

Biochemical synthesis

The formation of guanidinoacetate in the mammalian organism is primarily in the kidneys by transfer of the guanidine group of L-arginine by the enzyme L -Arg: Gly- amidinotransferase ( AGAT ) to the amino acid glycine. From L -Arg as produced ornithine, which is metabolized by Carbamoylation to citrulline in the urea cycle.

In a further step, GAA - methylated with S-adenosylmethionine through the enzyme guanidinoacetate N- methyltransferase ( GAMT ), creatine - in mammals in the liver. The creatine is released in the bloodstream.

Chemical Synthesis

Guanidinoacetic was first made ​​in 1861 by M. Strecker reaction of cyanamide with glycine in aqueous solution:

With S- methylisothiourea or with O- alkylisoureas as guanylating glycine can also be converted to GAA.

Recent patent literature describes the synthesis of ATM by catalytic oxidation of ethanolamine to glycine, followed by reaction with cyanamide in aqueous solution in high yield similar to the synthesis of creatine from N- methylaminoethanol about sarcosine

This route suppresses the formation of toxicologically critical Dihydrotriazins and other undesirable by-products such as iminodiacetic acid.

Properties

Guanidinoacetic acid is obtained as a white ( yellowish ) fine powder is granulated to improve handling, metering and recording with starch to form aggregates with an average diameter of 200-400 microns. The granulate is a long-term stable storage form for GAA. The resistance of guanidinoacetate in acidic aqueous solution is substantially higher than that of creatine, which cyclizes to creatinine under acid catalysis.

Use

Guanidinoacetic is an approved by the European Food Safety Authority (EFSA ) for the poultry production under the brand name CreAmino ® feed additive, even at low dosage (600 g / ton of feed) for " vegetarian diet", ie without feeding of animal protein should lead to higher feed efficiency, weight gain and improved muscle meat approach.

Advantages of a GAA supplementation in other breeding, fattening and domestic animals, as well as analogous to the GAA metabolite creatine in high-performance athletes can not yet be conclusively assessed. Co-administration of methyl group -donating substances such as Betaine is appropriate because of the danger of the formation of homocysteine ​​in our sole GAA administration.