Alanine
IUPAC name Alanine
Other names 2-Aminopropanoic acid
Identifiers
CAS number	338-69-2 (D-isomer) Y, 56-41-7 (L-isomer), 302-72-7 (racemic)
PubChem	5950
ChemSpider	64234 (D-isomer) Y, 5735 (L-isomer), 582 (Racemic)
UNII	1FU7983T0U N
EC-number	206-126-4
KEGG	C01401 N
ChEBI	CHEBI:57416 Y
ChEMBL	CHEMBL66693 Y
IUPHAR ligand	720
Jmol-3D images	Image 1 Image 2
SMILES O=C(O)C(N)C O=C(O)[C@H](N)C
InChI InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m1/s1 Y Key: QNAYBMKLOCPYGJ-UWTATZPHSA-N Y InChI=1/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6) Key: QNAYBMKLOCPYGJ-UHFFFAOYAA
Properties
Molecular formula	C3H7NO2
Molar mass	89.09 g mol−1
Appearance	white powder
Density	1.424 g/cm3
Melting point	258 °C, 531 K, 496 °F (subl.)
Solubility in water	167.2 g/L (25 °C)
Acidity (pKa)	2.35 (carboxyl), 9.69 (amino)[1]
Supplementary data page
Structure and properties	n, εr, etc.
Thermodynamic data	Phase behaviour Solid, liquid, gas
Spectral data	UV, IR, NMR, MS
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Alanine (abbreviated as Ala or A)^[2] is an α-amino acid with the chemical formula CH₃CH(NH₂)COOH. The L-isomer is one of the 20 amino acids encoded by the genetic code. Its codons are GCU, GCC, GCA, and GCG. It is classified as a nonpolar amino acid. L-Alanine is second only to leucine in rate of occurrence, accounting for 7.8% of the primary structure in a sample of 1,150 proteins.^[3] D-Alanine occurs in bacterial cell walls and in some peptide antibiotics.

Structure[link]

The α-carbon atom of alanine is bound with a methyl group (-CH₃), making it one of the simplest α-amino acids with respect to molecular structure and also resulting in alanine's being classified as an aliphatic amino acid. The methyl group of alanine is non-reactive and is thus almost never directly involved in protein function.

Sources[link]

Dietary sources[link]

Alanine is a nonessential amino acid, meaning it can be manufactured by the human body, and does not need to be obtained directly through the diet. Alanine is found in a wide variety of foods, but is particularly concentrated in meats.

Good sources of alanine include

• Animal sources: meat, seafood, caseinate, dairy products, eggs, fish, gelatin, lactalbumin
• Vegetarian sources: beans, nuts, seeds, soy, whey, brewer's yeast, brown rice, bran, corn, legumes, whole grains.

Biosynthesis[link]

Alanine can be manufactured in the body from pyruvate and branched chain amino acids such as valine, leucine, and isoleucine.

Alanine is most commonly produced by reductive amination of pyruvate. Because transamination reactions are readily reversible and pyruvate pervasive, alanine can be easily formed and thus has close links to metabolic pathways such as glycolysis, gluconeogenesis, and the citric acid cycle. It also arises together with lactate and generates glucose from protein via the alanine cycle.

Chemical synthesis[link]

Racemic alanine can be prepared by the condensation of acetaldehyde with ammonium chloride in the presence of sodium cyanide by the Strecker reaction, or by the ammonolysis of 2-bromopropanoic acid:^[4]

Physiological function[link]

Glucose–alanine cycle[link]

Alanine plays a key role in glucose–alanine cycle between tissues and liver. In muscle and other tissues that degrade amino acids for fuel, amino groups are collected in the form of glutamate by transamination. Glutamate can then transfer its amino group through the action of alanine aminotransferase to pyruvate, a product of muscle glycolysis, forming alanine and α-ketoglutarate. The alanine formed is passed into the blood and transported to the liver. A reverse of the alanine aminotransferase reaction takes place in liver. Pyruvate regenerated forms glucose through gluconeogenesis, which returns to muscle through the circulation system. Glutamate in the liver enters mitochondria and degrades into ammonium ion through the action of glutamate dehydrogenase, which in turn participate in the urea cycle to form urea.^[5]

The glucose–alanine cycle enables pyruvate and glutamate to be removed from the muscle and find their way to the liver. Glucose is regenerated from pyruvate and then returned to muscle: the energetic burden of gluconeogenesis is thus imposed on the liver instead of the muscle. All available ATP in muscle is devoted to muscle contraction.^[5]

Link to hypertension[link]

An international study led by Imperial College London found a correlation between high levels of alanine and higher blood pressure, energy intake, cholesterol levels, and body mass index.^[6]

(S)-Alanine (left) and (R)-alanine (right) in zwitterionic form at neutral pH

Link to Diabetes[link]

Alterations in the alanine cycle that increase the levels of serum alanine aminotransferase (ALT) is linked to the development of type II diabetes. With an elevated level of ALT the risk of developing type II diabetes increases.^[7]

Chemical properties[link]

Free radical stability[link]

The deamination of an alanine molecule produces a stable alkyl free radical, CH₃C^•HCOO^–. Deamination can be induced in solid or aqueous alanine by radiation.^[8]

This property of alanine is used in dosimetric measurements in radiotherapy. When normal alanine is irradiated, the radiation causes certain alanine molecules to become free radicals, and, as these radicals are stable, the free radical content^{[citation needed]} can later be measured in order to find out how much radiation the alanine was exposed to. In this way, one can be assured that complex radiotherapy treatment plans will deliver the intended pattern of radiation dose.

See also[link]

• Carbamic acid
• Glycine

References[link]

José Antonio Reyes

Reyes in action for Sevilla
Personal information
Full name	José Antonio Reyes Calderón
Date of birth	(1983-09-01) 1 September 1983 (age 28)
Place of birth	Utrera, Spain
Height	1.75 m (5 ft 9 in)
Playing position	Winger
Club information
Current club	Sevilla
Number	21
Youth career
1994–1999	Sevilla
Senior career*
Years	Team	Apps†	(Gls)†
1999–2001	Sevilla B	32	(1)
2000–2004	Sevilla	86	(21)
2004–2007	Arsenal	69	(16)
2006–2007	→ Real Madrid (loan)	30	(6)
2007–2011	Atlético Madrid	103	(8)
2008–2009	→ Benfica (loan)	26	(4)
2012–	Sevilla	19	(1)
National team
1999–2000	Spain U16	7	(5)
2001–2002	Spain U19	7	(3)
2002–2003	Spain U21	7	(3)
2003–2006	Spain	21	(4)
* Senior club appearances and goals counted for the domestic league only and correct as of 13 May 2012. † Appearances (Goals).

José Antonio Reyes Calderón (born 1 September 1983) is a Spanish professional footballer who plays for Sevilla FC, mainly as a left winger but also as a forward.

He made his professional debuts for hometown's Sevilla at only 16, signing for England's Arsenal aged 20. After a relatively successful career abroad, he returned to his country, going on to represent both main sides in Madrid, Real and Atlético, also having a short loan spell in Portugal with Benfica.

Reyes gained 21 caps for Spain, and represented the nation at the 2006 World Cup.

Club career[link]

Early career[link]

Born in Utrera, south-east Seville, to Spanish Kale (Gitanos) parents,^[1][2][3] Reyes joined the youth ranks of local Sevilla FC at the age of 10. His talent was identified, and he represented the club at all youth levels.

He finally signed a full contract in 1999, making his full squad debuts during 1999–2000 at just 16, in a game against Real Zaragoza, and was later called up to Spain's squad for the UEFA European Under-17 Football Championship. With the Andalusians now in Segunda División, he added another first-team club appearance.

After Sevilla promoted, Reyes established his reputation as a versatile offensive unit in the following years, his 22 goals in 86 matches over four seasons at Sevilla leading to other clubs taking notice, although the player's popularity with the club's fans made a move to a bigger Spanish club politically difficult for Sevilla's club president.

Arsenal[link]

Despite Sevilla manager Joaquín Caparrós wishing to hang onto him, Reyes signed with English club Arsenal during the January transfer window of the 2003–04 season. The £10.5 million transfer fee was negotiated with top ups, depending on the success of Arsenal, which could have risen to £17 million.^[4]

He made his debut on 1 February 2004 in a 2–1 win over Manchester City. Two days later, he scored an own goal against Middlesbrough in the Football League Cup. Later that month, Reyes netted twice against Chelsea to knock them out of the FA Cup; he also scored against the latter opponent in the season's UEFA Champions League quarterfinals, and his goals in the penultimate two games of the season helped keep Arsenal's unbeaten run in the Premier League going.

Hat-tricks in friendlies during the summer 2004 showed Reyes' improvement, and Reyes was a prominent influence on Arsenal's impressive start to the 2004–05 season, in which he managed to score in each of the first six games. However, he struggled during the middle of the season after Arsenal's defeat by Manchester United at Old Trafford. His inconsistent performance brought little reward for much of the season, and yet towards the end of it he scored three valuable goals.

In early 2005, Reyes was reported to be homesick while at Arsenal, even though his parents, Mari and Francisco, as well as brother Jesús lived with him in England. During a prank call perpetrated by Cadena COPE Radio of Spain in February 2005, a prankster claiming to be Emilio Butragueño, at the time director of football of Real Madrid, speaking on behalf of the president of the club, reportedly called Reyes' agent and spoke to Reyes himself about a possible transfer deal. In the ensuing conversation, Reyes allegedly declared that life in London was far from what he had envisioned and he would welcome a move back to his native Spain. Reyes also supposedly said that he wanted out of the club as there were "bad people" at Arsenal.^[5]

On 21 May 2005, Reyes became only the second player in history (after Kevin Moran) to be sent off in an FA Cup final, when he was dismissed for a second yellow card shortly before the end of extra time against Manchester United, though Arsenal still went on to win the game in a penalty shootout.

He temporarily ended speculation about a move away from Highbury in July 2005, when he signed a new six-year contract and declared that he was "looking forward to having many more successful years at the club." ^[6]

In Arsenal's 2005–06 Champions League run, Reyes featured heavily against, among others, Real Madrid, Juventus and Villarreal CF in the most impressive Champions League results for Arsenal to date. He came on as a substitute in the 17 May 2006 final against FC Barcelona, which Arsenal lost 2–1. However, in August 2006, he expressed a desire not to play in Arsenal's Champions League qualifying match against NK Dinamo Zagreb – to do so would render him 'cup-tied' and complicate a move to Real Madrid.^[7] Club manager Arsène Wenger left him out of the team, thus fuelling speculation that a transfer was soon to be agreed.

Real Madrid[link]

Reyes was linked to Real Madrid along with Arsenal teammate Cesc Fàbregas in the summer of 2006, when the candidate Arturo Baldasano of the then on-going Real Madrid presidential campaign claimed he would sign them, if elected.^[8] Reyes further hinted towards a transfer to Real. After making two official statements on Arsenal's website denying media reports of being unhappy, alleged quotes from Reyes in the Spanish press contradicted his denials. This tested the patience of Wenger, who reacted angrily to Real Madrid's attempts to unsettle his player, suggesting that it was not the first time Real Madrid had used the media and agents in Spain as a destabilising tactic. Shortly before the closure of the 2006 summer transfer window, Madrid and Arsenal agreed to exchange Reyes for Brazilian international Júlio Baptista, each on a season-long loan deal.^[9]

Reyes scored his first goal for Real Madrid on 17 September 2006, with a free kick against Real Sociedad, in a 2–0 home win. On the final day of the season, the focus was on soon-to-be-departed David Beckham and Roberto Carlos, but Reyes, brought from the bench for injured Beckham, netted twice as Real came from behind to beat RCD Mallorca and claim yet another La Liga title.

Real Madrid appointed former Getafe CF coach Bernd Schuster on 8 July 2007, increasing the chances that Reyes would sign a permanent deal and stay in Spain.^[10]

Atlético Madrid[link]

Reyes playing for Atlético Madrid in 2011

However, reports surfacing on 29 July indicated that city-rivals Atlético Madrid were on the verge of landing the player. Later that day, Wenger confirmed that Reyes' departure was imminent, and that a more specific announcement would be made shortly.^[11] On 30 July, Reyes passed his medical, penning a four-year deal, reportedly worth €12 million.^[12] He made his club debut against S.S. Lazio, scoring and assist once in a 3–1 victory in the annual Amsterdam Tournament (while at Arsenal, he was named the tournament's MVP in its 2004 edition). Reyes' first campaign with the Colchoneros was disastrous, as he was often kept out of the side by Maxi Rodríguez and Simão Sabrosa, and failed to score a single goal in 26 league appearances.

On 8 August 2008, S.L. Benfica announced the signing of Reyes on a one-year loan deal. The Portuguese also bought 25% of his playing rights for a fee of €2.65 million, and ensured a buying option of the remainder 75% for an undisclosed fee. He made his debut in a friendly match against Feyenoord. He replaced Jonathan Urretavizcaya in the 79th minute and, a minute afterwards, following a cross from Ariza Makukula, he made a volley which hit the post. His debut goal for Benfica was scored against city-rivals Sporting Clube de Portugal on 28 September 2008: after an understanding between Reyes and Pablo Aimar, and a pass from the same, he scored in fashion. Later in the same week, he would score again against S.S.C. Napoli, helping Benfica to a 2–0 home triumph in the season's UEFA Cup first round – the Reds eventually won 4–3 on aggregate.

Reyes' return to Atlético proved to be much more successful, as he re-united with Quique Flores, his manager at Benfica from the previous season. He scored his first official goal in Spain in more than two years on 9 January 2010, with a long-range effort at Real Valladolid, in a 4–0 triumph. By then, he had beaten the competition of Maxi and started in the wings alongside Simão. On 14 February 2010, Reyes put in a Man of the match performance in Atlético's 2–1 win against FC Barcelona,^[13] setting up the opening goal for Diego Forlán in the eventual champions' only league defeat of the season. Four days later, in the Europa League 1–1 home draw against Galatasaray SK, he scored a stunning free kick from the right wing on the 22nd minute, after he was brought down just outside the box (3–2 aggregate win). On 28 March, he curled in a left-footed shot from the right wing just inside the box, opening the score in the Madrid derby against his former team, in an eventual 2–3 loss.

On 27 August 2010, Reyes opened the score in the 2010 UEFA Super Cup against F.C. Internazionale Milano (eventually 2–0 win), after a one-two combination with Argentine Sergio Agüero.^[14] His first league goal of the season came in a 1–4 defeat at Hércules CF on 9 January 2011,^[15] which inspired an impressive run of scoring form, with goals in successive home games in February/March, against Valencia CF,^[16] former club Sevilla^[17] and Villarreal CF.^[18]

Reyes took up more responsibility for the 2011–12 campaign, and established himself as one of the team's most important players. On 28 July 2011, he scored twice for Atlético in a 2–1 Europa League win against Strømsgodset IF.^[19] In the second leg, a week later, he was again on the scoresheet, also assisting a goal for Adrián López in a 2–0 away success.^[20] However, he struggled to find the consistency he had under Flores and, after a fall out with new manager Gregorio Manzano after being subsitututed in a 0–3 defeat at Athletic Bilbao, his playing time became more and more limited.^[21][22]

Return to Sevilla[link]

On 5 January 2012, Sevilla confirmed the signing of Reyes, who penned a contract until June 2015.^[23] He played his first game three days later, starting in a 1–2 away loss against Rayo Vallecano.^[24] Reyes scored his first goal in his second spell in Sevilla, in 5 May in a 5-2 win against Rayo Vallecano.

International career[link]

Reyes earned his first full cap for Spain on 6 September 2003, replacing Raúl during a 3–0 friendly win in Portugal; he would be left out of Iñaki Sáez's UEFA Euro 2004 squad.

Two years later, he was picked for the 2006 FIFA World Cup, but only appeared once in four matches – the 1–0 group stage win against Saudi Arabia, with Spain already qualified as first.

Reyes was again overlooked for the victorious Euro 2008 tournament, as manager Luis Aragonés preferred the likes of David Silva and Santi Cazorla on the wings.

International Goals

#	Date	Venue	Opponent	Score	Result	Competition
1.	11 October 2003	Vazgen Sargsyan, Yerevan, Armenia	Armenia	0–3	0–4	Euro 2004 qualifying
2.	11 October 2003	Vazgen Sargsyan, Yerevan, Armenia	Armenia	0–4	0–4	Euro 2004 qualifying
3.	1 March 2006	José Zorrilla, Valladolid, Spain	Côte d'Ivoire	2–2	3–2	Friendly
4.	3 June 2006	Manuel Martínez Valero, Elche, Spain	Egypt	2–0	2–0	Friendly

Statistics[link]

Club[link]

(correct as of 28 August 2011)

International[link]

Honours[link]

Sevilla

• Second Division: 2000–01

Arsenal

• Premier League: 2003–04
• FA Cup: 2004–05
• FA Community Shield: 2004

Real Madrid

• Spanish League: 2006–07

Benfica

• Portuguese League Cup: 2008–09

Atlético Madrid

• UEFA Europa League: 2009–10, 2011–12
• UEFA Super Cup: 2010
• Spanish Cup: Runner-up 2009–10

Spain U-19

• UEFA European Under-19 Football Championship: 2002

References[link]

External links[link]

• Atlético Madrid official profile
• BDFutbol profile
• José Antonio Reyes career stats at Soccerbase
• Stats and profile at Zerozero
• National team data (Spanish)
• José Antonio Reyes at National-Football-Teams.com
• José Antonio Reyes – FIFA competition record
• Transfermarkt profile

v t e Spain squad – 2006 FIFA World Cup 1 Casillas 2 Salgado 3 Pernía 4 Marchena 5 Puyol 6 Albelda 7 Raúl (c) 8 Xavi 9 F. Torres 10 Reyes 11 Luis García 12 A. López 13 Iniesta 14 Alonso 15 Ramos 16 Senna 17 Joaquín 18 Fàbregas 19 Cañizares 20 Juanito 21 Villa 22 Ibáñez 23 Reina Coach: Aragonés

This article relies on references to primary sources or sources affiliated with the subject, rather than references from independent authors and third-party publications. Please add citations from reliable sources. (December 2007)

Rich Gaspari (born May 16, 1963) is an American former professional bodybuilder from 1980s and early 1990s. Gaspari was inducted into the IFBB Hall of Fame in 2004. Gaspari started his own supplement company Gaspari Nutrition. The company was formed in 2001 and includes the popular bodybuilding supplements "IntraPro", "SuperPump250" and "SizeOn".

In 2011, actor Ryan Phillippe and boxer Shane Mosley presented Gaspari with the Muscle Beach Hall of Fame Award.^[1] Gaspari was featured on the cover of the October, 2011 issue of Iron Man (magazine), 23 years after he last appeared on the cover of the magazine.^[2]

Personal life[link]

Gaspari was born in New Brunswick, New Jersey. He is a resident of Jackson Township, New Jersey.^[3]

Competition history[link]

• 1983 NPC Junior Nationals Overall Winner
• 1983 NPC Junior Nationals HeavyWeight, 1st
• 1983 NPC Nationals HeavyWeight, 5th
• 1984 NPC Nationals Light-HeavyWeight, 1st
• 1984 World IFBB Amateur Championships Light-HeavyWeight, 1st
• 1985 IFBB Night of Champions 2nd
• 1985 IFBB Mr. Olympia 3rd
• 1986 IFBB Los Angeles Pro Championships Winner
• 1986 IFBB Mr. Olympia 2nd
• 1986 IFBB World Pro Championships Winner
• 1987 IFBB Grand Prix France Winner
• 1987 IFBB Grand Prix Germany 2nd
• 1987 IFBB Grand Prix Germany (2) Winner
• 1987 IFBB Mr. Olympia 2nd
• 1988 IFBB Grand Prix England 2nd
• 1988 IFBB Grand Prix France Winner
• 1988 IFBB Grand Prix Germany Winner
• 1988 IFBB Grand Prix Greece 2nd
• 1988 IFBB Grand Prix Italy Winner
• 1988 IFBB Grand Prix Spain (2) 2nd
• 1988 IFBB Grand Prix Spain Winner
• 1988 IFBB Mr. Olympia 2nd
• 1989 IFBB Arnold Classic Winner
• 1989 IFBB Mr. Olympia 4th
• 1990 IFBB Mr. Olympia 5th
• 1991 IFBB Arnold Classic 7th
• 1991 IFBB Mr. Olympia 10th
• 1992 IFBB Arnold Classic 13th
• 1994 IFBB Chicago Pro Invitational 16th
• 1994 IFBB Niagara Falls Pro Invitational 15th
• 1994 IFBB Night of Champions - Did not place
• 1995 IFBB Canada Pro Cup 5th
• 1995 IFBB Night of Champions 12th
• 1996 IFBB Canada Pro Cup 11th
• 1996 IFBB Florida Pro Invitational 12th
• 1996 IFBB San Jose Pro Invitational 16th

References[link]

External links[link]

• Official Website
• Muscle Memory
• Rich Gaspari Profile