Isovaline L

• CAT Number: I029613
• CAS Number: 595-40-4
• Molecular Formula: C55H11NO2
• Molecular Weight: 117.15
• Purity: 98%
• Synonyms: Isovaline L-; NSC 1019; NSC-1019; NSC1019
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
• IUPAC Name: Isovaline, L- (8CI)
• InChI: InChI=1S/C5H11NO2/c1-3-5(2,6)4(7)8/h3,6H2,1-2H3,(H,7,8)/t5-/m1/s1
• InChIKey: GCHPUFAZSONQIV-RXMQYKEDSA-N
• SMILES: N[C@@](C(O)=O)(CC)C

Isovaline L (Cat.No:I029613) is an amino acid derivative that belongs to the group of non-proteinogenic amino acids. It is structurally similar to the natural amino acid valine but contains an additional methyl group. Isovaline L- has been studied for its potential use in peptide synthesis and as a building block for the development of novel pharmaceutical compounds.

Reference

1: Kojo S. S-Isovaline Contained in Meteorites, Induces Enantiomeric Excess in D,L-glutamic Acid During Recrystallization. Orig Life Evol Biosph. 2015 Jun;45(1-2):85-91. doi: 10.1007/s11084-015-9407-8. Epub 2015 Mar 11. PubMed PMID: 25754590.
2: Dutt Konar A, Vass E, Hollósi M, Majer Z, Grüber G, Frese K, Sewald N. Conformational properties of secondary amino acids: replacement of pipecolic acid by N-methyl-l-alanine in efrapeptin C. Chem Biodivers. 2013 May;10(5):942-51. doi: 10.1002/cbdv.201300086. PubMed PMID: 23681735.
3: De Zotti M, Schievano E, Mammi S, Kaptein B, Broxterman QB, Singh SB, Brückner H, Toniolo C. Configurational assignment of D- and L-isovalines in intact, natural, and synthetic peptides by 2D-NMR spectroscopy. Chem Biodivers. 2010 Jun;7(6):1612-24. doi: 10.1002/cbdv.200900287. PubMed PMID: 20564673.
4: MacDermott AJ, Fu T, Nakatsuka R, Coleman AP, Hyde GO. Parity-violating energy shifts of Murchison L-amino acids are consistent with an electroweak origin of meteorite L-enantiomeric excesses. Orig Life Evol Biosph. 2009 Oct;39(5):459-78. doi: 10.1007/s11084-009-9162-9. Epub 2009 Mar 24. Erratum in: Orig Life Evol Biosph. 2009 Dec;39(6):599. PubMed PMID: 19308669.
5: Glavin DP, Dworkin JP. Enrichment of the amino acid L-isovaline by aqueous alteration on CI and CM meteorite parent bodies. Proc Natl Acad Sci U S A. 2009 Apr 7;106(14):5487-92. doi: 10.1073/pnas.0811618106. Epub 2009 Mar 16. PubMed PMID: 19289826; PubMed Central PMCID: PMC2667035.
6: Vandenabeele-Trambouze O, Geffard M, Bodet D, Despois M, Dobrijevic M, Loustalot MF, Commeyras A. Antibodies directed against L and D isovaline using a chemical derivatizing reagent for the measurement of their enantiomeric ratio in extraterrestrial samples: first step-production and characterization of antibodies. Chirality. 2002 Jun;14(6):519-26. PubMed PMID: 12112348.
7: Bonner WA. The radiolysis and radioracemization of poly-L-leucines. Radiat Res. 1999 Jul;152(1):83-7. PubMed PMID: 10381845.
8: Kawai M, Omori Y, Yamamura H, Butsugan Y, Taga T, Miwa Y. Crystal structures of Boc-D- and L-Iva-L-Pro-OBzl: unturned conformation of Aib-Pro sequence unaffected by replacement of Me with Et in Aib. Biopolymers. 1993 Aug;33(8):1207-12. PubMed PMID: 8364155.