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Alanine

History and Etymology of Alanine: – Alanine was first synthesized in 1850 by Adolph Strecker. – Named Alanin in German for ease of pronunciation. – […]

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History and Etymology of Alanine:
– Alanine was first synthesized in 1850 by Adolph Strecker.
– Named Alanin in German for ease of pronunciation.
– The naming referenced aldehyde.
– The German ending -in is analogous to English -ine.

Structure and Synthesis:
– Alanine is an aliphatic amino acid with a methyl side-chain.
– It is the simplest α-amino acid after glycine.
– Nonessential and can be synthesized by the body.
– Produced from pyruvate and certain amino acids.
– Industrially produced by decarboxylation of aspartate.

Physiological Function and Cycle:
– Key role in the glucose–alanine cycle.
– Transfer of amino groups between tissues and the liver.
– Alanine aminotransferase reaction occurs in reverse in the liver.
– Linked to type II diabetes and gluconeogenesis in the liver.

Alanine World Hypothesis and Protein Structures:
– One of the earliest amino acids in the genetic code.
– Explains evolutionary choice of amino acids.
– Used in alanine scanning mutagenesis.
– Key amino acid in protein sequences and metabolism of D-amino acids.

Dosimetry, Research, and Biochemical Studies:
– Alanine dosimetry used in ionizing radiation measurement.
– Role in radiotherapy dosimetry audits.
– Studies on amino acid evolution, genetic code development, and prebiotic amino acid synthesis.
– Nitrogen metabolism and excretion studies involving alanine aminotransferase.

Alanine (Wikipedia)

Alanine (symbol Ala or A), or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side chain. Consequently it is classified as a nonpolar, aliphatic α-amino acid. Under biological conditions, it exists in its zwitterionic form with its amine group protonated (as −NH3+) and its carboxyl group deprotonated (as −CO2). It is non-essential to humans as it can be synthesized metabolically and does not need to be present in the diet. It is encoded by all codons starting with GC (GCU, GCC, GCA, and GCG).

Alanine
Alanine in non-ionic form
Skeletal formula of L-alanine (neutral form)
Ball-and-stick model (zwitterionic form)
Space-filling model (zwitterionic form)
Names
IUPAC name
Alanine
Systematic IUPAC name
2-Aminopropanoic acid
Other names
Alanic acid
Alaninic acid
2-Aminopropionic acid
Identifiers
3D model (JSmol)
3DMet
1720248
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.000.249 Edit this at Wikidata
EC Number
  • L: 206-126-4
49628
KEGG
UNII
  • InChI=1S/C3H7NO2/c1-2(4)3(5)6/h2H,4H2,1H3,(H,5,6)/t2-/m0/s1
    Key: QNAYBMKLOCPYGJ-REOHCLBHSA-N checkY
  • D/L: Key: QNAYBMKLOCPYGJ-UHFFFAOYSA-N
  • D: Key: QNAYBMKLOCPYGJ-UWTATZPHSA-N
  • L: C[C@@H](C(=O)O)N
  • D: C[C@H](C(=O)O)N
  • L Zwitterion: C[C@@H](C(=O)[O-])[NH3+]
  • D Zwitterion: C[C@H](C(=O)[O-])[NH3+]
Properties
C3H7NO2
Molar mass 89.094 g·mol−1
Appearance white powder
Density 1.424 g/cm3
Melting point 258 °C (496 °F; 531 K) (sublimes)
167.2 g/L (25 °C)
log P -0.68
Acidity (pKa)
  • 2.34 (carboxyl; H2O)
  • 9.87 (amino; H2O)
-50.5·10−6 cm3/mol
Supplementary data page
Alanine (data page)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

The L-isomer of alanine (left-handed) is the one that is incorporated into proteins. L-alanine is second only to L-leucine in rate of occurrence, accounting for 7.8% of the primary structure in a sample of 1,150 proteins. The right-handed form, D-alanine, occurs in peptides in some bacterial cell walls (in peptidoglycan) and in some peptide antibiotics, and occurs in the tissues of many crustaceans and molluscs as an osmolyte.

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