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32467-88-2-Acv tripeptide Acv tripeptide

Acv tripeptide

For research use only. Not for therapeutic Use.

  • CAT Number: I021342
  • CAS Number: 32467-88-2
  • Molecular Formula: C14H25N3O6S
  • Molecular Weight: 363.43
  • Purity: 98%
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Acv tripeptide (Cat.No:I021342), also known as Acetyl-valyl-valyl-seryl-alanine or Ac-Val-Val-Ser-Ala, is a small peptide that has been shown to have anti-inflammatory and antioxidant properties. It has been studied for its potential therapeutic applications in various inflammatory conditions and neurodegenerative disorders. Acv tripeptide is synthesized by enzymatic processes.


Catalog Number I021342
CAS Number 32467-88-2
Synonyms

Acv tripeptide; Acv [MI]; Tripeptides, acv;

Molecular Formula C14H25N3O6S
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years).
IUPAC Name (S)-2-amino-6-(((R)-1-(((R)-1-carboxy-2-methylpropyl)amino)-3-mercapto-1-oxopropan-2-yl)amino)-6-oxohexanoic acid
InChI InChI=1S/C14H25N3O6S/c1-7(2)11(14(22)23)17-12(19)9(6-24)16-10(18)5-3-4-8(15)13(20)21/h7-9,11,24H,3-6,15H2,1-2H3,(H,16,18)(H,17,19)(H,20,21)(H,22,23)/t8-,9-,11+/m0/s1
InChIKey BYEIJZFKOAXBBV-ATZCPNFKSA-N
SMILES CC(C)[C@H](C(O)=O)NC([C@H](CS)NC(CCC[C@H](N)C(O)=O)=O)=O
Reference

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6: Daruzzaman A, Clifton IJ, Adlington RM, Baldwin JE, Rutledge PJ. The interaction of isopenicillin N synthase with homologated substrate analogues δ-(L-α-aminoadipoyl)-L-homocysteinyl-D-Xaa characterised by protein crystallography. Chembiochem. 2013 Mar 18;14(5):599-606. doi: 10.1002/cbic.201200728. Epub 2013 Mar 6. PubMed PMID: 23468426.
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8: Fernández-Aguado M, Teijeira F, Martín JF, Ullán RV. A vacuolar membrane protein affects drastically the biosynthesis of the ACV tripeptide and the beta-lactam pathway of Penicillium chrysogenum. Appl Microbiol Biotechnol. 2013 Jan;97(2):795-808. doi: 10.1007/s00253-012-4256-0. Epub 2012 Jul 11. PubMed PMID: 22777282.
9: Wu X, García-Estrada C, Vaca I, Martín JF. Motifs in the C-terminal region of the Penicillium chrysogenum ACV synthetase are essential for valine epimerization and processivity of tripeptide formation. Biochimie. 2012 Feb;94(2):354-64. doi: 10.1016/j.biochi.2011.08.002. Epub 2011 Aug 27. PubMed PMID: 21889568.
10: Clifton IJ, Ge W, Adlington RM, Baldwin JE, Rutledge PJ. Isopenicillin N synthase binds δ-(L-α-aminoadipoyl)-L-cysteinyl-D-thia-allo-isoleucine through both sulfur atoms. Chembiochem. 2011 Aug 16;12(12):1881-5. doi: 10.1002/cbic.201100149. Epub 2011 Jun 15. PubMed PMID: 21678539.
11: Martín JF, Ullán RV, García-Estrada C. Regulation and compartmentalization of β-lactam biosynthesis. Microb Biotechnol. 2010 May;3(3):285-99. doi: 10.1111/j.1751-7915.2009.00123.x. Epub 2009 May 31. Review. PubMed PMID: 21255328; PubMed Central PMCID: PMC3815371.
12: Ge W, Clifton IJ, Stok JE, Adlington RM, Baldwin JE, Rutledge PJ. Crystallographic studies on the binding of selectively deuterated LLD- and LLL-substrate epimers by isopenicillin N synthase. Biochem Biophys Res Commun. 2010 Aug 6;398(4):659-64. doi: 10.1016/j.bbrc.2010.06.129. Epub 2010 Jul 13. PubMed PMID: 20603104.
13: Ge W, Clifton IJ, Stok JE, Adlington RM, Baldwin JE, Rutledge PJ. The crystal structure of an LLL-configured depsipeptide substrate analogue bound to isopenicillin N synthase. Org Biomol Chem. 2010 Jan 7;8(1):122-7. doi: 10.1039/b910170e. Epub 2009 Oct 29. PubMed PMID: 20024142.
14: Ge W, Clifton IJ, Howard-Jones AR, Stok JE, Adlington RM, Baldwin JE, Rutledge PJ. Structural studies on the reaction of isopenicillin N synthase with a sterically demanding depsipeptide substrate analogue. Chembiochem. 2009 Aug 17;10(12):2025-31. doi: 10.1002/cbic.200900080. PubMed PMID: 19598184.
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16: Ge W, Clifton IJ, Stok JE, Adlington RM, Baldwin JE, Rutledge PJ. Isopenicillin N synthase mediates thiolate oxidation to sulfenate in a depsipeptide substrate analogue: implications for oxygen binding and a link to nitrile hydratase? J Am Chem Soc. 2008 Aug 6;130(31):10096-102. doi: 10.1021/ja8005397. Epub 2008 Jul 12. PubMed PMID: 18620394.
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18: Long AJ, Clifton IJ, Roach PL, Baldwin JE, Rutledge PJ, Schofield CJ. Structural studies on the reaction of isopenicillin N synthase with the truncated substrate analogues delta-(L-alpha-aminoadipoyl)-L-cysteinyl-glycine and delta-(L-alpha-aminoadipoyl)-L-cysteinyl-D-alanine. Biochemistry. 2005 May 3;44(17):6619-28. PubMed PMID: 15850395.
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