N-Valyltryptophan

• CAT Number: I033713
• CAS Number: 24587-37-9
• Molecular Formula: C16H21N3O3
• Molecular Weight: 303.36
• Purity: 98%
• Synonyms: N-Valyltryptophan; Val-trp; L-Valyl-L-tryptophan
• 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: L-valyl-L-tryptophan
• InChI: InChI=1S/C16H21N3O3/c1-9(2)14(17)15(20)19-13(16(21)22)7-10-8-18-12-6-4-3-5-11(10)12/h3-6,8-9,13-14,18H,7,17H2,1-2H3,(H,19,20)(H,21,22)/t13-,14-/m0/s1
• InChIKey: LZDNBBYBDGBADK-KBPBESRZSA-N
• SMILES: O=C(O)[C@H](CC1=CNC2=C1C=CC=C2)NC([C@H](C(C)C)N)=O

N-Valyltryptophan is a dipeptide composed of valine and tryptophan. It is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis.

Reference

1: Li Y, Wang F, Zhang PZ, Yang M. [Chemical Constituents from Periplaneta americana]. Zhong Yao Cai. 2015 Oct;38(10):2038-41. Chinese. PubMed PMID: 27254913.
2: Lunow D, Kaiser S, Rückriemen J, Pohl C, Henle T. Tryptophan-containing dipeptides are C-domain selective inhibitors of angiotensin converting enzyme. Food Chem. 2015 Jan 1;166:596-602. doi: 10.1016/j.foodchem.2014.06.059. Epub 2014 Jun 18. PubMed PMID: 25053098.
3: Boudesocque L, Kapel R, Paris C, Dhulster P, Marc I, Renault JH. Concentration and selective fractionation of an antihypertensive peptide from an alfalfa white proteins hydrolysate by mixed ion-exchange centrifugal partition chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2012 Sep 15;905:23-30. doi: 10.1016/j.jchromb.2012.07.034. Epub 2012 Aug 3. PubMed PMID: 22939269.
4: Hatanaka A, Miyahara H, Suzuki KI, Sato S. Isolation and identification of antihypertensive peptides from antarctic krill tail meat hydrolysate. J Food Sci. 2009 May-Jul;74(4):H116-20. doi: 10.1111/j.1750-3841.2009.01138.x. PubMed PMID: 19490329.
5: Holden HM, Matthews BW. The binding of L-valyl-L-tryptophan to crystalline thermolysin illustrates the mode of interaction of a product of peptide hydrolysis. J Biol Chem. 1988 Mar 5;263(7):3256-60. PubMed PMID: 3343246.