Dehydroalanine

Dehydroalanine
IUPAC name 2-Aminoprop-2-enoic acid
Identifiers
CAS number	1948-56-7
PubChem	123991
ChemSpider	110510 Y
DrugBank	DB02688
KEGG	C02218 Y
ChEBI	CHEBI:17123 Y
Jmol-3D images	Image 1 Image 2
SMILES C=C(C(=O)O)N O=C(O)C(=C)N
InChI InChI=1S/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6) Y Key: UQBOJOOOTLPNST-UHFFFAOYSA-N Y InChI=1/C3H5NO2/c1-2(4)3(5)6/h1,4H2,(H,5,6) Key: UQBOJOOOTLPNST-UHFFFAOYAW
Properties
Molecular formula	C3H5NO2
Molar mass	87.08 g/mol
Y (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

Dehydroalanine (or (alpha)-(beta)-di-dehydroalanine) is an uncommon amino acid found in peptides of microbial origin (an unsaturated amino acid).

Dehydroalanine (DHA) is also found in food proteins, including casein, that have been heated and/or treated with an alkali such as sodium hydroxide (NaOH). These treatments can dehydrate serine in the protein chain. In food, DHA frequently alkylates lysine to yield the crosslinking aminoacid lysinoalanine (LAL). Lysinoalanine, N6-(DL-2-amino-2-carboxyethyl)-L-lysine, an unusual amino acid implicated as a renal toxic factor in laboratory rats (kidney damage), has been found in proteins of home-cooked and commercial foods and ingredients. Although it had been reported to occur in both edible and non-food proteins only after alkali treatment (such as occurs in soybean processing), it has also been identified in food proteins that had not been subjected to alkali. Lysinoalanine can also be generated in a variety of proteins when heated under non-alkaline conditions.

Many dehydroalanine-containing peptides are toxic or antibiotic and constitute parts of lantibiotics or microcystins.

See also

• Lanthionine

References

PubChem 123991

This article about an amine is a stub. You can help Wikipedia by expanding it.v · Categories: Amino acids Amine stubs Wikimedia Foundation. 2010. Игры ⚽ Поможем написать реферат Oakley Tian Look at other dictionaries: dehydroalanine — noun An uncommon amino acid found in peptides of microbial origin …   Wiktionary Amino acid — This article is about the class of chemicals. For the structures and properties of the standard proteinogenic amino acids, see Proteinogenic amino acid. The generic structure of an alpha amino acid in its unionized form …   Wikipedia Lanthionine — Chembox new Name = Lanthionine ImageFile = Lanthionine.png Section1 = Chembox Identifiers PubChem = 675804 CASNo = 922 55 4 Section2 = Chembox Properties Formula = C6H12N2O4S MolarMass = 208.2318 g/mol MeltingPt = 280 283 °CLanthionine is a… …   Wikipedia Lantibiotics — are a class of peptide antibiotics that contain polycyclic thioether amino acids as well as the unsaturated amino acids dehydroalanine and 2 aminoisobutyric acid. These characteristic cyclic thioether amino acids are composed of either… …   Wikipedia Microcystin — Chemical structure of Microcystin LR Microcystins are cyclic nonribosomal peptides produced by cyanobacteria (e.g.Microcystis aeruginosa). They are cyanotoxins and can be very toxic for plants and animals including humans. Their hepatotoxicity… …   Wikipedia Nonribosomal peptide — Nonribosomal peptides (NRP) are a class of peptide secondary metabolites, usually produced by microorganisms like bacteria and fungi. Nonribosomal peptides are also found in higher organisms, such as nudibranchs, but are thought to be made by… …   Wikipedia Chemical biology — is a scientific discipline spanning the fields of chemistry and biology that involves the application of chemical techniques and tools, often compounds produced through synthetic chemistry, to the study and manipulation of biological systems.… …   Wikipedia 3-Dehydroquinic acid — IUPAC name (1R,3R,4S) 1,3,4 trihydroxy 5 oxocyclohexanecarboxylic acid …   Wikipedia Microcystine — La microcystine est le type de cyanotoxine le plus étudié à ce jour, et contenant plus de soixante dix variantes[1]. Cette molécule est constituée de sept acides aminés qui se rejoignent aux extrémités pour former une structure cyclique …   Wikipédia en Français lantibiotic — noun Any of a class of peptide antibiotics that contain polycyclic thioether amino acids as well as the unsaturated amino acids dehydroalanine and 2 aminoisobutyric acid …   Wiktionary 18+ © Academic, 2000-2024 Contact us: Technical Support, Advertising Dictionaries export, created on PHP, Joomla, Drupal, WordPress, MODx. Mark and share Search through all dictionaries Translate… Search Internet Share the article and excerpts Direct link … Do a right-click on the link above and select “Copy Link”