3-aminopropionic acid

3-アミノプロピオン酸

WordNet

1. street name for lysergic acid diethylamide (同)back breaker, battery-acid, dose, dot, Elvis, loony toons, Lucy in the sky with diamonds, pane, superman, window pane, Zen
2. any of various water-soluble compounds having a sour taste and capable of turning litmus red and reacting with a base to form a salt
3. having the characteristics of an acid; "an acid reaction"

PrepTutorEJDIC

1. 酸性の / 酸味のある,すっぱい(sour) / (言葉・態度などが)厳しい,しんらつな / 酸 / すっぱいもの / 《俗》=LSD

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/12/24 06:11:23」(JST)

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β-Alanine

Names
IUPAC name 3-Aminopropanoic acid
Other names β-Alanine 3-Aminopropionic acid
Identifiers
CAS Number	107-95-9 Y
ChEBI	CHEBI:16958 Y
ChEMBL	ChEMBL297569 Y
ChemSpider	234 Y
DrugBank	DB03107 Y
EC Number	203-536-5
IUPHAR/BPS	2365
Jmol interactive 3D	Image
KEGG	D07561 Y
PubChem	239
UNII	11P2JDE17B Y
InChI InChI=1S/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6) Y Key: UCMIRNVEIXFBKS-UHFFFAOYSA-N Y InChI=1/C3H7NO2/c4-2-1-3(5)6/h1-2,4H2,(H,5,6) Key: UCMIRNVEIXFBKS-UHFFFAOYAL
SMILES O=C(O)CCN
Properties
Chemical formula	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)
Solubility in water	54.5 g/100 mL
Solubility	soluble in methanol. diethyl ether, acetone
log P	-3.05
Acidity (pKa)	3.63
Hazards
Main hazards	Irritant
Safety data sheet	[1]
NFPA 704	1 2 0
Lethal dose or concentration (LD, LC):
LD50 (Median dose)	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.

β-Alanine is not used in the biosynthesis of any major proteins or enzymes. It is formed in vivo by the degradation of dihydrouracil and carnosine. 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. 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. Simply supplementing with carnosine is not as effective as supplementing with β-alanine alone since carnosine, when taken by mouth, is simply broken down during digestion to its components, histidine and beta-alanine. This results in only about 40% of the total dose being available as beta-alanine.

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

Typically, studies have used supplementing strategies of multiple doses of 400 mg or 800 mg, administered at regular intervals for up to eight hours, over periods ranging from 4 to 10 weeks. After a 10-week supplementing strategy, the reported increase in intramuscular carnosine content was an average of 80.1% (range 18 to 205%).

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, 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), 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.

Free β-Alanine can cause paraesthesia, a form of neuropathic pain, when ingested in amounts above 10 mg per kilogram of body weight. This is variable between individuals: mild symptoms are experienced by some individuals at 10 mg per kg of body weight; are significant in a majority at 20 mg per kg of body weight; and are severe at 40 mg/kg.

It is probable that the paraesthesia results from high peak blood-plasma concentrations of β-alanine, since an equivalent (equimolar) amount of β-alanine to 40 mg per kg of body weight did not cause paraesthesia when ingested in the form of histidine-containing dipeptides (i.e., carnosine and anserine) in chicken broth extract. In this case, the β-alanine absorption profile is flattened but sustained for a longer period of time, whereas the β-alanine samples in the sports supplementation studies was administered as the free amino acid, resulting in the rapid rise of plasma concentrations, peaking within 30 to 45 minutes, and being eliminated after 90 to 120 minutes. The paraesthesia is not necessary for efficacy, since the published studies undertaken so far have utilized doses of 400 mg or 800 mg at a time to avoid the paraesthesia. Furthermore, excretion of β-alanine in urine accounted for 0.60%(+/-0.09), 1.50%(+/-0.40), or 3.64%(+/-0.47) of the administered doses of 10, 20, or 40 mg per kg body weight, indicating greater losses occurring with increasing dosage.

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).

A high-potency artificial sweetener, called suosan, is derived from beta-alanine.

References

External links

• KEGG map of β-alanine metabolism
• International Society of Sports Nutrition Conference Proceedings

UpToDate Contents

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English Journal

• The beneficial effects of Momordica charantia (bitter gourd) on wound healing of rabbit skin.

• Pişkin A1, Altunkaynak BZ, Tümentemur G, Kaplan S, Yazıcı OB, Hökelek M.Author information 1Departments of Orthopedic and Trauma Surgery, Medical School of Ondokuz Mayıs University , Samsun , Turkey.AbstractMomordica charantia (MC; bitter gourd) is a traditional herbal commonly used for its antidiabetic, antioxidant, contraceptive and antibacterial properties. In the current study, the authors aim to observe the topical effect of MC cream on the wound-healing process in rabbits. Moreover, they compare the healing potential with conventional creams used therapeutically. Towards this aim, 28 New Zealand rabbits were divided into four groups and excision wounds (7 cm²) were made on their backs. Open wound dressing was carried out daily for 28 days among the experimental groups with the application of dekspanthenol (Bepanthen®; BP group, n = 7), nitrofurazon (Furacin®; FR group, n = 7) and olive oil extract of MC (MC group, n = 7). No application was made to the control group. At the end of day 28, areas of the skin with initial wound area were en bloc dissected and prepared for histopathological and stereological analysis. Inflammatory cells were abundant in the control group and cream application led to a decrease in the number of these cells, especially in the MC group. The highest number of fibroblasts was detected in the MC group. Furthermore, the MC group displayed the highest fractions of epidermis to papillary dermis, fibroblasts to reticular dermis and collagen fibres to reticular dermis. The MC group also presented a high density of blood vessels, moderate density of collagen fibres and mature fibroblasts. The BP group showed better epithelialisation compared with the FR group, but the latter provided more effective reorganisation of the dermis. Different cream supplements caused healthy and fast wound healing according to untreated controls and the results show that administration of the MC extract improves and accelerates the process of wound healing in rabbits in comparison with the BP and FR extracts.
• The Journal of dermatological treatment.J Dermatolog Treat.2014 Aug;25(4):350-7. doi: 10.3109/09546634.2012.713459. Epub 2012 Sep 21.
• Momordica charantia (MC; bitter gourd) is a traditional herbal commonly used for its antidiabetic, antioxidant, contraceptive and antibacterial properties. In the current study, the authors aim to observe the topical effect of MC cream on the wound-healing process in rabbits. Moreover, they compare
• PMID 22812507

• Synthesis, crystal growth and spectroscopic investigation of novel metal organic crystal: β-Alanine cadmium bromide monohydrate (β-ACBM).

• Renugadevi R1, Kesavasamy R2.Author information 1Department of Physics, SriGuru Institute of Technology, Coimbatore 641110, India.2Department of Physics, Sri Ramakrishna Engineering College, Coimbatore 641020, India. Electronic address: kesav_cbe@yahoo.co.in.Abstractβ-Alanine cadmium bromide monohydrate (β-ACBM), a new metal organic crystal has been grown from aqueous solution by slow evaporation technique. The grown crystals have been subjected to single crystal X-ray diffraction analysis to determine the crystal structure. The β-ACBM crystallized in monoclinic system with space group P21/c. The presence of protons and carbons in the β-alanine cadmium bromide monohydrate was confirmed by (1)H and (13)C nuclear magnetic resonance spectral analysis. The mode of vibration of different molecular groups present in β-ACBM was identified by FT-IR spectral analysis. Transparency of crystals in UV-Vis-NIR region has also been studied. The thermal characteristics of as-grown crystals were analyzed using thermo gravimetric and differential thermal analyses. The magnetic property of the grown crystal was investigated using Vibrating Sample Magnetometer (VSM) at ambient temperature. The mechanical stability of β-ACBM was evaluated by Vickers microhardness measurement.
• Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2014 Jul 15;128:622-8. doi: 10.1016/j.saa.2014.03.005. Epub 2014 Mar 18.
• β-Alanine cadmium bromide monohydrate (β-ACBM), a new metal organic crystal has been grown from aqueous solution by slow evaporation technique. The grown crystals have been subjected to single crystal X-ray diffraction analysis to determine the crystal structure. The β-ACBM crystallized in monocl
• PMID 24691377

• Influence of training status on high-intensity intermittent performance in response to β-alanine supplementation.

• de Salles Painelli V1, Saunders B, Sale C, Harris RC, Solis MY, Roschel H, Gualano B, Artioli GG, Lancha AH Jr.Author information 1Laboratory of Applied Nutrition and Metabolism, School of Physical Education and Sport, University of Sao Paulo, Av. Mello de Moraes, 65-Butanta, São Paulo, SP, 05508-030, Brazil.AbstractRecent investigations have suggested that highly trained athletes may be less responsive to the ergogenic effects of β-alanine (BA) supplementation than recreationally active individuals due to their elevated muscle buffering capacity. We investigated whether training status influences the effect of BA on repeated Wingate performance. Forty young males were divided into two groups according to their training status (trained: T, and non-trained: NT cyclists) and were randomly allocated to BA and a dextrose-based placebo (PL) groups, providing four experimental conditions: NTPL, NTBA, TPL, TBA. BA (6.4 g day(-1)) or PL was ingested for 4 weeks, with participants completing four 30-s lower-body Wingate bouts, separated by 3 min, before and after supplementation. Total work done was significantly increased following supplementation in both NTBA (p = 0.03) and TBA (p = 0.002), and it was significantly reduced in NTPL (p = 0.03) with no difference for TPL (p = 0.73). BA supplementation increased mean power output (MPO) in bout 4 for the NTBA group (p = 0.0004) and in bouts 1, 2 and 4 for the TBA group (p ≤ 0.05). No differences were observed in MPO for NTPL and TPL. BA supplementation was effective at improving repeated high-intensity cycling performance in both trained and non-trained individuals, highlighting the efficacy of BA as an ergogenic aid for high-intensity exercise regardless of the training status of the individual.
• Amino acids.Amino Acids.2014 May;46(5):1207-15. doi: 10.1007/s00726-014-1678-2. Epub 2014 Feb 6.
• Recent investigations have suggested that highly trained athletes may be less responsive to the ergogenic effects of β-alanine (BA) supplementation than recreationally active individuals due to their elevated muscle buffering capacity. We investigated whether training status influences the effect o
• PMID 24500111

Japanese Journal

• Incorporation of Fluorescent-Labeled Non-.ALPHA.-Amino Carboxylic Acids into the N-Terminus of Proteins in Response to Amber Initiation Codon

• Bulletin of the Chemical Society of Japan 83(5), 546-553, 2010
• NAID 130004152733

• 42 ブレオマイシンの制癌機構解明への合成的研究 : 軸配位子および連結部位の役割(口頭発表の部)

• 天然有機化合物討論会講演要旨集 (33), 321-328, 1991-09-07
• NAID 110006679010

• Recovery of individual metals from gallium-arsenic-indium semiconductor wastes by flotation.

• Analytical Sciences 6(5), 783-784, 1990
• NAID 130003529021

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3-アミノプロピオン酸 3-aminopropionic acid