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Anserine information


Anserine
Names
Systematic IUPAC name
(Z)-N-(3-Amino-1-hydroxypropylidene)-3-methyl-L-histidine
Other names
beta-Alanyl-3-methyl-L-histidine
Identifiers
CAS Number
  • 584-85-0 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:18323 checkY
ChEMBL
  • ChEMBL448301 checkY
ChemSpider
  • 100482 checkY
ECHA InfoCard 100.008.679 Edit this at Wikidata
KEGG
  • C01262 checkY
PubChem CID
  • 112072
UNII
  • HDQ4N37UGV checkY
CompTox Dashboard (EPA)
  • DTXSID30973950 Edit this at Wikidata
InChI
  • InChI=1S/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1 checkY
    Key: MYYIAHXIVFADCU-QMMMGPOBSA-N checkY
  • InChI=1/C10H16N4O3/c1-14-6-12-5-7(14)4-8(10(16)17)13-9(15)2-3-11/h5-6,8H,2-4,11H2,1H3,(H,13,15)(H,16,17)/t8-/m0/s1
    Key: MYYIAHXIVFADCU-QMMMGPOBBJ
SMILES
  • O=C(O)[C@@H](NC(=O)CCN)Cc1cncn1C
Properties
Chemical formula
C10H16N4O3
Molar mass 240.25904 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Anserine (β-alanyl-3-methylhistidine) is a dipeptide containing β-alanine and 3-methylhistidine.[1] Anserine is a derivative of carnosine, which has been methylated.[2]

Both anserine and carnosine chelate copper.[3] Due to its methylation, anserine is more stable in serum and resistant to degradation than carnosine.[4] Anserine can be found in the skeletal muscle and brain of mammals and birds.[2]

The pKa of the imidazole ring of histidine, when contained in anserine, is 7.04.[5][6]

  1. ^ Garrett CM, Grisham RH (2012). Biochemistry (5th ed.). Cengage Learning. p. 46. ISBN 978-1-133-10629-6.
  2. ^ a b Blancquaert L, Baba SP, Kwiatkowski S, Stautemas J, Stegen S, Barbaresi S, Chung W, Boakye AA, Hoetker JD, Bhatnagar A, Delanghe J (2016-09-01). "Carnosine and anserine homeostasis in skeletal muscle and heart is controlled by β-alanine transamination". The Journal of Physiology. 594 (17): 4849–4863. doi:10.1113/JP272050. ISSN 1469-7793. PMC 5009790. PMID 27062388.
  3. ^ Cite error: The named reference :3 was invoked but never defined (see the help page).
  4. ^ Everaert I, Baron G, Barbaresi S, Gilardoni E, Coppa C, Carini M, Vistoli G, Bex T, Stautemas J, Blancquaert L, Derave W (January 2019). "Development and validation of a sensitive LC-MS/MS assay for the quantification of anserine in human plasma and urine and its application to pharmacokinetic study". Amino Acids. 51 (1): 103–114. doi:10.1007/s00726-018-2663-y. hdl:2434/599742. ISSN 1438-2199. PMID 30302566. S2CID 52945820.
  5. ^ Wu G (March 2020). "Important roles of dietary taurine, creatine, carnosine, anserine and 4-hydroxyproline in human nutrition and health". Amino Acids. 52 (3): 329–360. doi:10.1007/s00726-020-02823-6. ISSN 1438-2199. PMC 7088015. PMID 32072297.
  6. ^ Cite error: The named reference :0 was invoked but never defined (see the help page).

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Anserine

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Anserine (β-alanyl-3-methylhistidine) is a dipeptide containing β-alanine and 3-methylhistidine. Anserine is a derivative of carnosine, which has been...

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Pes anserine bursitis

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Pes anserine bursitis is an inflammatory condition of the medial (inner) knee at the anserine bursa, a sub muscular bursa, just below the pes anserinus...

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Anserine bursa

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The anserine bursa (tibial intertendinous bursa) is a sub muscular bursa located deep to the pes anserinus on the anteromedial proximal tibia. Pes anserine...

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Anatidae

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of Pirəkəşkül, Azerbaijan) – anserine or Pelagornithidae (same as Caspiodontornis?) Chenornis (Early Miocene) – anserine or Phalacrocoracidae Paranyroca...

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Traumatic anserine folliculosis

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Traumatic anserine folliculosis is a curious gooseflesh-like follicular hyperkeratosis that may result from persistent pressure and lateral friction of...

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Bursitis

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Retrocalcaneal bursitis Ischial bursitis, "weaver's bottom" Iliopsoas bursitis Anserine bursitis It is important to differentiate between infected and non-infected...

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Carnosine

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exercise. Acetylcarnosine, a similar molecule used to treat lens cataracts Anserine, another dipeptide antioxidant (found in birds) Carnosine synthase, an...

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Sartorius muscle

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of the many conditions that can disrupt the use of the sartorius is pes anserine bursitis, an inflammatory condition of the medial portion of the knee....

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Acronym

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transcription activator), HET-E (incompatibility locus protein from Podospora anserine), and TP1 (telomerase-associated protein) – but is not syntactically reducible...

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Trauma

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that results from the forceful pulling out of the scalp hair Traumatic anserine folliculosis, a curious gooseflesh-like follicular hyperkeratosis Traumatic...

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List of Germanic and Latinate equivalents in English

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sheep/ovine, swan/cygnine or cygnean, duck/anatine, starling/sturnine, goose/anserine, horse/equine, chicken/gallinaceous, cow/bovine, pig/porcine, whale/cetacean...

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List of animal names

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(on land) skein (in flight) team (in flight) wedge (in flight) anatine anserine poultry Gorilla infant — blackback silverback band troop, group whoop simian...

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Dipeptide

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ester) is an artificial sweetener. Carnosine (beta-alanyl-L-histidine) and Anserine (beta-alanyl-N-methyl histidine) are highly concentrated in muscle and...

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Lutra

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of amphibians (mainly frogs and pond turtles), bird predation (mainly anserine species), small rodents, and invertebrates such as water beetles, snails...

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Prepatellar bursitis

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when irritated, as their walls are very thin.: p. 22  Along with the pes anserine bursa, the prepatellar bursa is one of the most common bursae to cause...

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Latin influence in English

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goat/caprine, sheep/ovine, swan/cygnean, duck/anatine, starling/sturnine, goose/anserine, ostrich/struthious, horse/equine, chicken/gallinaceous, ox/bovine, pig/porcine...

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Knee bursae

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between the medial head of the gastrocnemius and the joint capsule the anserine bursa between the medial (tibial) collateral ligament and the pes anserinus...

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Carnosine synthase

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Other names in common use include 'carnosine synthetase', 'carnosine-anserine synthetase', 'homocarnosine synthetase', and 'carnosine-homocarnosine synthetase'...

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List of Latin words with English derivatives

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superannuate, superannuation, triennial, triennium ānser ānser- goose Anser, anserine †anserculus ansercul- gosling antenna antenn- antenna, antennal, antennule...

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Body odor

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neuropathica Poliosis Rubinstein–Taybi syndrome Setleis syndrome Traumatic anserine folliculosis Trichomegaly Trichomycosis axillaris Trichorrhexis (Trichorrhexis...

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List of skin conditions

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effluvium Terry's nails Traction alopecia Traumatic alopecia Traumatic anserine folliculosis Triangular alopecia (temporal alopecia, temporal triangular...

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PES

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varus (pes varus), varus deformity of the foot Pes anserinus (leg) Pes anserine bursitis, inflammatory of the inner knee at the bursa of the pes anserinus...

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