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Wikipedia

Sepiapterin

Sepiapterin, also known as 2-amino-6-[(2S)-2-hydroxypropanoyl]-7,8-dihydro-1H-pteridin-4-one, is a member of the pteridine class of organic chemicals.

l-Sepiapterin
Names
IUPAC name
2-amino-6-[(2S)-2-hydroxypropanoyl]-7,8-dihydro-1H-pteridin-4-one
Identifiers
  • 17094-01-8 Y
3D model (JSmol)
  • Interactive image
ChEMBL
  • ChEMBL1255653 N
ChemSpider
  • 58746 Y
KEGG
  • C00835 Y
  • 65253
UNII
  • CJQ26KO7HP Y
  • InChI=1S/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1 Y
    Key: VPVOXUSPXFPWBN-VKHMYHEASA-N Y
  • InChI=1/C9H11N5O3/c1-3(15)6(16)4-2-11-7-5(12-4)8(17)14-9(10)13-7/h3,15H,2H2,1H3,(H4,10,11,13,14,17)/t3-/m0/s1
    Key: VPVOXUSPXFPWBN-VKHMYHEABT
  • O=C1\N=C(/NC=2NCC(=N/C1=2)\C(=O)[C@@H](O)C)N
Properties
C9H11N5O3
Molar mass 237.22 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Sepiapterin can be metabolized into tetrahydrobiopterin via a salvage pathway. Tetrahydrobiopterin is an essential cofactor in humans for breakdown of phenylalanine and a catalyst of the metabolism of phenylalanine, tyrosine, and tryptophan to precursors of the neurotransmitters dopamine and serotonin.

Deficiency of tetrahydrobiopterin can cause toxic buildup of phenylalanine (phenylketonuria) as well as deficiencies of dopamine, norepinephrine, and epinephrine, leading to dystonia and other neurological illnesses. This has led to clinical study of sepiapterin in humans to treat tetrahydrobiopterin deficiency.[1]

Since atherosclerosis and other circulatory diseases associated with diabetes are also associated with tetrahydrobiopterin deficiency, animal studies of the value of sepiaterin in these vascular diseases have been done. These studies show that relaxation of the blood vessels studied was impaired after animals were given sepiapterin, even though their levels of tetrahydrobiopterin were replenished.[2]

See also edit

References edit

  1. ^ Smith, Neil; Longo, Nicola; Levert, Keith; Hyland, Keith; Blau, Nenad (1 April 2019). "Phase I clinical evaluation of CNSA-001 (sepiapterin), a novel pharmacological treatment for phenylketonuria and tetrahydrobiopterin deficiencies, in healthy volunteers". Molecular Genetics and Metabolism. 126 (4): 406–412. doi:10.1016/j.ymgme.2019.02.001. ISSN 1096-7192. PMID 30922814. S2CID 85564348.
  2. ^ Vasquez-Vivar, Jeannette; Duquiane, Damon; Whitsett, Jennifer; Kalyanaraman, B.; Rajagopalan, Sanjay (1 October 2002). "Altered Tetrahydrobiopterin Metabolism in Atherosclerosis". Arteriosclerosis, Thrombosis, and Vascular Biology. 22 (10): 1655–1661. doi:10.1161/01.ATV.0000029122.79665.D9. PMID 12377745.


sepiapterin, also, known, amino, hydroxypropanoyl, dihydro, pteridin, member, pteridine, class, organic, chemicals, namesiupac, name, amino, hydroxypropanoyl, dihydro, pteridin, oneidentifierscas, number, 17094, model, jsmol, interactive, imagechembl, chembl12. Sepiapterin also known as 2 amino 6 2S 2 hydroxypropanoyl 7 8 dihydro 1H pteridin 4 one is a member of the pteridine class of organic chemicals l Sepiapterin NamesIUPAC name 2 amino 6 2S 2 hydroxypropanoyl 7 8 dihydro 1H pteridin 4 oneIdentifiersCAS Number 17094 01 8 Y3D model JSmol Interactive imageChEMBL ChEMBL1255653 NChemSpider 58746 YKEGG C00835 YPubChem CID 65253UNII CJQ26KO7HP YInChI InChI 1S C9H11N5O3 c1 3 15 6 16 4 2 11 7 5 12 4 8 17 14 9 10 13 7 h3 15H 2H2 1H3 H4 10 11 13 14 17 t3 m0 s1 YKey VPVOXUSPXFPWBN VKHMYHEASA N YInChI 1 C9H11N5O3 c1 3 15 6 16 4 2 11 7 5 12 4 8 17 14 9 10 13 7 h3 15H 2H2 1H3 H4 10 11 13 14 17 t3 m0 s1Key VPVOXUSPXFPWBN VKHMYHEABTSMILES O C1 N C NC 2NCC N C1 2 C O C H O C NPropertiesChemical formula C9H11N5O3Molar mass 237 22 g molExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Sepiapterin can be metabolized into tetrahydrobiopterin via a salvage pathway Tetrahydrobiopterin is an essential cofactor in humans for breakdown of phenylalanine and a catalyst of the metabolism of phenylalanine tyrosine and tryptophan to precursors of the neurotransmitters dopamine and serotonin Deficiency of tetrahydrobiopterin can cause toxic buildup of phenylalanine phenylketonuria as well as deficiencies of dopamine norepinephrine and epinephrine leading to dystonia and other neurological illnesses This has led to clinical study of sepiapterin in humans to treat tetrahydrobiopterin deficiency 1 Since atherosclerosis and other circulatory diseases associated with diabetes are also associated with tetrahydrobiopterin deficiency animal studies of the value of sepiaterin in these vascular diseases have been done These studies show that relaxation of the blood vessels studied was impaired after animals were given sepiapterin even though their levels of tetrahydrobiopterin were replenished 2 See also editDihydrobiopterin Tetrahydrobiopterin Dystonia Phenylketonuria Salvage pathwayReferences edit Smith Neil Longo Nicola Levert Keith Hyland Keith Blau Nenad 1 April 2019 Phase I clinical evaluation of CNSA 001 sepiapterin a novel pharmacological treatment for phenylketonuria and tetrahydrobiopterin deficiencies in healthy volunteers Molecular Genetics and Metabolism 126 4 406 412 doi 10 1016 j ymgme 2019 02 001 ISSN 1096 7192 PMID 30922814 S2CID 85564348 Vasquez Vivar Jeannette Duquiane Damon Whitsett Jennifer Kalyanaraman B Rajagopalan Sanjay 1 October 2002 Altered Tetrahydrobiopterin Metabolism in Atherosclerosis Arteriosclerosis Thrombosis and Vascular Biology 22 10 1655 1661 doi 10 1161 01 ATV 0000029122 79665 D9 PMID 12377745 nbsp This article about a ketone is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Sepiapterin amp oldid 1198220564, wikipedia, wiki, book, books, library,

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