''β''-Alanine

β-Alanine
Skeletal formula of beta alanine
Ball-and-stick model of the β-alanine molecule as a zwitterion
Names
IUPAC name
3-Aminopropanoic acid
Other names
β-Alanine
3-Aminopropionic acid
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.003.215
EC Number 203-536-5
KEGG
UNII
Properties[1][2]
C3H7NO2
Molar mass 89.093 g/mol
Appearance white bipyramidal crystals
Odor odorless
Density 1.437 g/cm3 (19 °C)
Melting point 207 °C (405 °F; 480 K) (decomposes)
54.5 g/100 mL
Solubility soluble in methanol. Insoluble in diethyl ether, acetone
log P -3.05
Acidity (pKa) 3.63
Hazards
Main hazards Irritant
Safety data sheet
NFPA 704
Flammability code 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g., canola oilHealth code 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g., chloroformReactivity code 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g., liquid nitrogenSpecial hazards (white): no codeNFPA 704 four-colored diamond
1
2
0
Lethal dose or concentration (LD, LC):
1000 mg/kg (rat, oral)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

β-Alanine (or beta-alanine) is a naturally occurring beta amino acid, which is an amino acid in which the amino group is at the β-position from the carboxylate group (i.e., two atoms away, see Figure 1). The IUPAC name for β-alanine is 3-aminopropanoic acid. Unlike its counterpart α-alanine, β-alanine has no stereocenter.

Biosynthesis and industrial route

In terms of its biosynthesis, it is formed by the degradation of dihydrouracil and carnosine. β-Alanine ethyl ester is the ethyl ester which hydrolyises within the body to form β-alanine.[3] It is produced industrially by the reaction of ammonia with β-propiolactone.[4]

Biochemical function

β-Alanine is not found in any major proteins or enzymes. It is a component of the naturally occurring peptides carnosine and anserine and also of pantothenic acid (vitamin B5), which itself is a component of coenzyme A. Under normal conditions, β-alanine is metabolized into acetic acid.

β-Alanine is the rate-limiting precursor of carnosine, which is to say carnosine levels are limited by the amount of available β-alanine, not histidine.[5] Supplementation with β-alanine has been shown to increase the concentration of carnosine in muscles, decrease fatigue in athletes and increase total muscular work done.[6][7] Simply supplementing with carnosine is not as effective as supplementing with β-alanine alone since carnosine, when taken orally, is broken down during digestion to its components, histidine and β-alanine. Hence, by weight, only about 40% of the dose is available as β-alanine.[5]

Figure 1: Comparison of β-alanine (right) with the more customary (chiral) amino acid, L-α-alanine (left)

L-Histidine, with a pKa of 6.1 is a relatively weak buffer over the physiological intramuscular pH range. However, when bound to other amino acids, this increases nearer to 6.8-7.0. In particular, when bound to β-alanine, the pKa value is 6.83,[8] making this a very efficient intramuscular buffer. Furthermore, because of the position of the beta amino group, β-alanine dipeptides are not incorporated into proteins, and thus can be stored at relatively high concentrations (millimolar). Occurring at 17–25 mmol/kg (dry muscle),[9] carnosine (β-alanyl-L-histidine) is an important intramuscular buffer, constituting 10-20% of the total buffering capacity in type I and II muscle fibres.

Even though much weaker than glycine (and, thus, with a debated role as a physiological transmitter), β-alanine is an agonist next in activity to the cognate ligand glycine itself, for strychnine-sensitive inhibitory glycine receptors (GlyRs) (the agonist order: glycine ≫ β-alanine > taurine ≫ alanine, L-serine > proline).[10]

Athletic performance enhancement

There is evidence that β-alanine supplementation can increase exercise performance, but there is concern about lack of information about safety.[11][12][13][14]

Ingestion of β-Alanine can cause paraesthesia, reported as a tingling sensation, in a dose-dependent fashion.[14]

Metabolism

Sources for β-alanine includes pyrimidine catabolism of cytosine and uracil.

β-alanine can undergo a transanimation reaction with pyruvate to form malonate-semialdehyde and L-alanine. The malonate semialdehyde can then be converted into malonate via malonate-semialdehyde dehydrogenase. Malonate is then converted into malonyl-CoA and enter fatty acid biosynthesis.[15]

Alternatively, β-alanine can be diverted into Pantothenate and Coenzyme A biosynthesis.[15]

References

  1. ↑ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals (11th ed.), Merck, 1989, ISBN 091191028X , 196.
  2. ↑ Weast, Robert C., ed. (1981). CRC Handbook of Chemistry and Physics (62nd ed.). Boca Raton, FL: CRC Press. p. C-83. ISBN 0-8493-0462-8. .
  3. ↑ Wright, Margaret Robson (1969). "Arrhenius parameters for the acid hydrolysis of esters in aqueous solution. Part I. Glycine ethyl ester, β-alanine ethyl ester, acetylcholine, and methylbetaine methyl ester". Journal of the Chemical Society B: Physical Organic: 707. doi:10.1039/J29690000707.
  4. ↑ Karlheinz Miltenberger "Hydroxycarboxylic Acids, Aliphatic" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2005. doi:10.1002/14356007.a13_507
  5. 1 2 "Beta-Alanine Supplementation For Exercise Performance". Retrieved 21 September 2018.
  6. ↑ Derave W, Ozdemir MS, Harris R, Pottier A, Reyngoudt H, Koppo K, Wise JA, Achten E (August 9, 2007). "Beta-alanine supplementation augments muscle carnosine content and attenuates fatigue during repeated isokinetic contraction bouts in trained sprinters". J Appl Physiol. 103 (5): 1736–43. doi:10.1152/japplphysiol.00397.2007. PMID 17690198.
  7. ↑ Hill CA, Harris RC, Kim HJ, Harris BD, Sale C, Boobis LH, Kim CK, Wise JA (2007). "Influence of beta-alanine supplementation on skeletal muscle carnosine concentrations and high intensity cycling capacity". Amino Acids. 32 (2): 225–33. doi:10.1007/s00726-006-0364-4. PMID 16868650.
  8. ↑ Bate-Smith, EC (1938). "The buffering of muscle in rigor: protein, phosphate and carnosine". Journal of Physiology. 92 (3): 336–343. PMC 1395289. PMID 16994977.
  9. ↑ Mannion, AF; Jakeman, PM; Dunnett, M; Harris, RC; Willan, PLT (1992). "Carnosine and anserine concentrations in the quadriceps femoris muscle of healthy humans". Eur. J. Appl. Physiol. 64: 47–50. doi:10.1007/BF00376439.
  10. ↑ Encyclopedia of Life Sciences Amino Acid Neurotransmitters. Jeremy M Henley, 2001 John Wiley & Sons, Ltd. doi:10.1038/npg.els.0000010, Article Online Posting Date: April 19, 2001
  11. ↑ Quesnele JJ, Laframboise MA, Wong JJ, Kim P, Wells GD (2014). "The effects of beta-alanine supplementation on performance: a systematic review of the literature". Int J Sport Nutr Exerc Metab (Systematic review). 24 (1): 14–27. doi:10.1123/ijsnem.2013-0007. PMID 23918656.
  12. ↑ Hoffman JR, Stout JR, Harris RC, Moran DS (2015). "β-Alanine supplementation and military performance". Amino Acids. 47 (12): 2463–74. doi:10.1007/s00726-015-2051-9. PMC 4633445. PMID 26206727.
  13. ↑ Hobson, R. M.; Saunders, B.; Ball, G.; Harris, R. C.; Sale, C. (9 December 2016). "Effects of β-alanine supplementation on exercise performance: a meta-analysis". Amino Acids. 43 (1): 25–37. doi:10.1007/s00726-011-1200-z. ISSN 0939-4451. PMC 3374095. PMID 22270875.
  14. 1 2 Trexler ET, Smith-Ryan AE, Stout JR, Hoffman JR, Wilborn CD, Sale C, Kreider RB, Jäger R, Earnest CP, Bannock L, Campbell B, Kalman D, Ziegenfuss TN, Antonio J (2015). "International society of sports nutrition position stand: Beta-Alanine". J Int Soc Sports Nutr (Review). 12: 30. doi:10.1186/s12970-015-0090-y. PMC 4501114. PMID 26175657.
  15. 1 2 "KEGG PATHWAY: beta-Alanine metabolism - Reference pathway". www.genome.jp. Retrieved 2016-10-04.
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