Glycine betaine aldehyde

Last updated
Glycine betaine aldehyde
Betaine aldehyde.svg
Names
IUPAC name
N,N,N-Trimethylglycinium
Systematic IUPAC name
N,N,N-Trimethyl-2-oxoethan-1-aminium
Other names
Betaine aldehyde
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
KEGG
PubChem CID
UNII
  • InChI=1/C5H12NO/c1-6(2,3)4-5-7/h5H,4H2,1-3H3/q+1
    Key: SXKNCCSPZDCRFD-UHFFFAOYAL
  • O=CC[N+](C)(C)C
Properties
C5H12NO
Molar mass 102.157 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Glycine betaine aldehyde, often simply called betaine aldehyde, [1] is an intermediate in the metabolism of glycine, serine and threonine. The human aldehyde dehydrogenase (EC 1.2.1.3) stimulates the transformation of betaine aldehyde to glycine betaine. Betaine aldehyde is a substrate for choline dehydrogenase (mitochondrial). [2]

Contents

Chemical structure

Glycine betaine aldehyde is a short chain aldehyde and quaternary ammonium compound. It can be considered a derivative of the amino acid glycine. Its chemical formula is C5H12NO+.

Biological function

Glycine betaine aldehyde is a component of glycine, serine and threonine metabolism. It also serves as an osmolyte.

It can be found in cytoplasm and mitochondria within the kidney, neurons, and stratum corneum. [3]

Related Research Articles

<span class="mw-page-title-main">Threonine</span> Amino acid

Threonine is an amino acid that is used in the biosynthesis of proteins. It contains an α-amino group, a carboxyl group, and a side chain containing a hydroxyl group, making it a polar, uncharged amino acid. It is essential in humans, meaning the body cannot synthesize it: it must be obtained from the diet. Threonine is synthesized from aspartate in bacteria such as E. coli. It is encoded by all the codons starting AC.

<span class="mw-page-title-main">Choline</span> Chemical compound and essential nutrient

Choline is a cation with the chemical formula [(CH3)3NCH2CH2OH]+. Choline forms various salts, for example choline chloride and choline bitartrate.

<span class="mw-page-title-main">Sarcosine</span> Chemical compound

Sarcosine, also known as N-methylglycine, or monomethylglycine, is a amino acid with the formula CH3N(H)CH2CO2H. It exists at neutral pH as the zwitterion CH3N+(H)2CH2CO2, which can be obtained as a white, water-soluble powder. Like some amino acids, sarcosine converts to a cation at low pH and an anion at high pH, with the respective formulas CH3N+(H)2CH2CO2H and CH3N(H)CH2CO2. Sarcosine is a close relative of glycine, with a secondary amine in place of the primary amine.

Lipotropic compounds are those that help catalyse the breakdown of fat during metabolism in the body. A lipotropic nutrient promotes or encourages the export of fat from the liver. Lipotropics are necessary for maintenance of a healthy liver, and for burning the exported fat for additional energy. Without lipotropics, such as choline and inositol, fats and bile can become trapped in the liver, causing severe problems such as cirrhosis and blocking fat metabolism.

<span class="mw-page-title-main">Trimethylglycine</span> Chemical compound

Trimethylglycine is an amino acid derivative that occurs in plants. Trimethylglycine was the first betaine discovered; originally it was simply called betaine because, in the 19th century, it was discovered in sugar beets.

<span class="mw-page-title-main">Amino acid synthesis</span> The set of biochemical processes by which amino acids are produced

Amino acid synthesis is the set of biochemical processes by which the amino acids are produced. The substrates for these processes are various compounds in the organism's diet or growth media. Not all organisms are able to synthesize all amino acids. For example, humans can synthesize 11 of the 20 standard amino acids. These 11 are called the non-essential amino acids).

<span class="mw-page-title-main">Serine hydroxymethyltransferase</span>

Serine hydroxymethyltransferase (SHMT) is a pyridoxal phosphate (PLP) (Vitamin B6) dependent enzyme (EC 2.1.2.1) which plays an important role in cellular one-carbon pathways by catalyzing the reversible, simultaneous conversions of L-serine to glycine and tetrahydrofolate (THF) to 5,10-Methylenetetrahydrofolate (5,10-CH2-THF). This reaction provides the largest part of the one-carbon units available to the cell.

<span class="mw-page-title-main">L-threonine 3-dehydrogenase</span> Class of enzymes

In enzymology, a L-threonine 3-dehydrogenase (EC 1.1.1.103) is an enzyme that catalyzes the chemical reaction

In enzymology, a (R)-aminopropanol dehydrogenase (EC 1.1.1.75) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Betaine—homocysteine S-methyltransferase</span> Class of enzymes

In the field of enzymology, a betaine-homocysteine S-methyltransferase also known as betaine-homocysteine methyltransferase (BHMT) is a zinc metallo-enzyme that catalyzes the transfer of a methyl group from trimethylglycine and a hydrogen ion from homocysteine to produce dimethylglycine and methionine respectively:

In enzymology, a choline monooxygenase (EC 1.14.15.7) is an enzyme that catalyzes the chemical reaction

In enzymology, a choline dehydrogenase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Choline oxidase</span>

In enzymology, a choline oxidase (EC 1.1.3.17) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Aspartate-semialdehyde dehydrogenase</span> Amino-acid-synthesizing enzyme in fungi, plants and prokaryota

In enzymology, an aspartate-semialdehyde dehydrogenase is an enzyme that is very important in the biosynthesis of amino acids in prokaryotes, fungi, and some higher plants. It forms an early branch point in the metabolic pathway forming lysine, methionine, leucine and isoleucine from aspartate. This pathway also produces diaminopimelate which plays an essential role in bacterial cell wall formation. There is particular interest in ASADH as disabling this enzyme proves fatal to the organism giving rise to the possibility of a new class of antibiotics, fungicides, and herbicides aimed at inhibiting it.

<span class="mw-page-title-main">Betaine-aldehyde dehydrogenase</span> Enzyme

In enzymology, a betaine-aldehyde dehydrogenase (EC 1.2.1.8) is an enzyme that catalyzes the chemical reaction

In enzymology, a dimethylglycine dehydrogenase (EC 1.5.8.4) is an enzyme that catalyzes the chemical reaction

In enzymology, a glycine dehydrogenase (cytochrome) (EC 1.4.2.1) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Threonine aldolase</span>

The enzyme threonine aldolase is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Glycocyamine</span> Chemical compound

Glycocyamine is a metabolite of glycine in which the amino group has been converted into a guanidine by guanylation. In vertebrate organism it is then transformed into creatine by methylation.

Carnitine biosynthesis is a method for the endogenous production of L-carnitine, a molecule that is essential for energy metabolism. In humans and many other animals, L-carnitine is obtained from both diet and by biosynthesis. The carnitine biosynthesis pathway is highly conserved among many eukaryotes and some prokaryotes.

References

  1. Betaine aldehyde Archived 2007-11-24 at the Wayback Machine , Biological Magnetic Resonance Data Bank
  2. Yilmaz JL, Bülow L. (December 2002). "Enhanced stress tolerance in Escherichia coli and Nicotiana tabacum expressing a betaine aldehyde dehydrogenase/choline dehydrogenase fusion protein". Biotechnol. Prog. 18 (6): 1176–82. doi:10.1021/bp020057k. PMID   12467448. S2CID   8054758.
  3. , Human Metabolome Database