Valylvaline | CAS#3918-94-3 | Mycoplasma genitalium metabolite

MedKoo Cat#: 598141 | Name: Valylvaline

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Valylvaline is a dipeptide formed from two L-valine residues. It has a role as a Mycoplasma genitalium metabolite. It is functionally related to a L-valine.

Chemical Structure

Valylvaline

CAS#3918-94-3

Theoretical Analysis

MedKoo Cat#: 598141

Name: Valylvaline

CAS#: 3918-94-3

Chemical Formula: C10H20N2O3

Exact Mass: 216.1474

Molecular Weight: 216.28

Elemental Analysis: C, 55.53; H, 9.32; N, 12.95; O, 22.19

Price and Availability

Size	Price	Availability
5mg	USD 75.00	Ready to ship
10mg	USD 110.00	Ready to ship
25mg	USD 210.00	Ready to ship
50mg	USD 350.00	Ready to ship
100mg	USD 550.00	Ready to ship
200mg	USD 950.00	Ready to ship

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Related CAS #

No Data

Synonym

Valylvaline; Val-val; H-VAL-VAL-OH; L-Valyl-L-valine

IUPAC/Chemical Name

L-valyl-L-valine

InChi Key

KRNYOVHEKOBTEF-YUMQZZPRSA-N

InChi Code

InChI=1S/C10H20N2O3/c1-5(2)7(11)9(13)12-8(6(3)4)10(14)15/h5-8H,11H2,1-4H3,(H,12,13)(H,14,15)/t7-,8-/m0/s1

SMILES Code

CC(C)[C@@H](C(O)=O)NC([C@H](C(C)C)N)=O

Appearance

Solid powder

Purity

>97% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot# A21M11B01

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Valylvaline is a secondary metabolite.

In vitro activity:

FT-IR spectroscopy and X-ray diffraction patterns revealed that the peptide fibers have parallel-type beta-sheet networks between the valylvaline units. Though dipeptide units have potential to take β-sheet, hexagonal, and random coil conformations, bulky isopropyl side chains of the valylvaline residues would enforce the β-sheet conformation rather than more closely-packed hexagonal lattice. Valylvaline residues form the parallel-type β-pleats-sheets at both sides of the bola-amphiphiles. Reference: Biochim Biophys Acta. 2000 Jul 26;1475(3):346-52. https://pubmed.ncbi.nlm.nih.gov/10913835/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	0.0	0.00

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 216.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Kogiso M, Okada Y, Hanada T, Yase K, Shimizu T. Self-assembled peptide fibers from valylvaline bola-amphiphiles by a parallel beta-sheet network. Biochim Biophys Acta. 2000 Jul 26;1475(3):346-52. doi: 10.1016/s0304-4165(00)00088-x. PMID: 10913835. 2. Tamura K, Bhatnagar PK, Takata JS, Lee CP, Smith PL, Borchardt RT. Metabolism, uptake, and transepithelial transport of the diastereomers of Val-Val in the human intestinal cell line, Caco-2. Pharm Res. 1996 Aug;13(8):1213-8. doi: 10.1023/a:1016068421243. PMID: 8865315.

In vitro protocol:

In vivo protocol:

TBD

1: Xu X, Sun L, Zhou L, Cheng Y, Cao F. Functional chitosan oligosaccharide nanomicelles for topical ocular drug delivery of dexamethasone. Carbohydr Polym. 2020 Jan 1;227:115356. doi: 10.1016/j.carbpol.2019.115356. Epub 2019 Sep 20. PMID: 31590850. 2: Yang X, Sheng Y, Ray A, Shah SJ, Trinh HM, Pal D, Mitra AK. Uptake and bioconversion of stereoisomeric dipeptide prodrugs of ganciclovir by nanoparticulate carriers in corneal epithelial cells. Drug Deliv. 2016 Sep;23(7):2532-2540. doi: 10.3109/10717544.2015.1023384. Epub 2015 Mar 16. PMID: 25775276. 3: Yang X, Shah SJ, Wang Z, Agrahari V, Pal D, Mitra AK. Nanoparticle-based topical ophthalmic formulation for sustained release of stereoisomeric dipeptide prodrugs of ganciclovir. Drug Deliv. 2016 Sep;23(7):2399-2409. doi: 10.3109/10717544.2014.996833. Epub 2015 Jan 7. PMID: 25564964. 4: Pal R, Reddy MB, Dinesh B, Balaram P, Guru Row TN. Temperature-induced reversible first-order single crystal to single crystal phase transition in Boc-γ(4)(R)Val-Val-OH: interplay of enthalpy and entropy. J Phys Chem A. 2014 Oct 9;118(40):9568-74. doi: 10.1021/jp506874q. Epub 2014 Sep 23. PMID: 25198546. 5: González-Castro TB, Nicolini H, Lanzagorta N, López-Narváez L, Genis A, Pool García S, Tovilla-Zárate CA. The role of brain-derived neurotrophic factor (BDNF) Val66Met genetic polymorphism in bipolar disorder: a case-control study, comorbidities, and meta-analysis of 16,786 subjects. Bipolar Disord. 2015 Feb;17(1):27-38. doi: 10.1111/bdi.12227. Epub 2014 Jul 8. PMID: 25041243. 6: Barot M, Gokulgandhi MR, Pal D, Mitra AK. Mitochondrial localization of P-glycoprotein and peptide transporters in corneal epithelial cells--novel strategies for intracellular drug targeting. Exp Eye Res. 2013 Jan;106:47-54. doi: 10.1016/j.exer.2012.10.006. Epub 2012 Oct 29. PMID: 23116562; PMCID: PMC3545686. 7: Gaudana R, Parenky A, Vaishya R, Samanta SK, Mitra AK. Development and characterization of nanoparticulate formulation of a water soluble prodrug of dexamethasone by HIP complexation. J Microencapsul. 2011;28(1):10-20. doi: 10.3109/02652048.2010.520093. Epub 2010 Oct 12. PMID: 20939702; PMCID: PMC4516232. 8: Yu H, Zhang Z, Shi Y, Bai F, Xie C, Qian Y, Yuan Y, Deng L. Association study of the decreased serum BDNF concentrations in amnestic mild cognitive impairment and the Val66Met polymorphism in Chinese Han. J Clin Psychiatry. 2008 Jul;69(7):1104-11. doi: 10.4088/jcp.v69n0710. PMID: 18505307. 9: Hagen K, Stovner LJ, Skorpen F, Pettersen E, Zwart JA. COMT genotypes and use of antipsychotic medication: linking population-based prescription database to the HUNT study. Pharmacoepidemiol Drug Saf. 2008 Apr;17(4):372-7. doi: 10.1002/pds.1567. PMID: 18302304. 10: Grdadolnik J, Grdadolnik SG, Avbelj F. Determination of conformational preferences of dipeptides using vibrational spectroscopy. J Phys Chem B. 2008 Mar 6;112(9):2712-8. doi: 10.1021/jp7096313. Epub 2008 Feb 9. PMID: 18260662. 11: Nath M, Pokharia S, Eng G, Song X, Kumar A. New triorganotin (IV) derivatives of dipeptides as models for metal-protein interactions: synthesis, structural characterization and biological studies. Spectrochim Acta A Mol Biomol Spectrosc. 2006 Jan;63(1):66-75. doi: 10.1016/j.saa.2005.04.038. Epub 2005 Jun 9. PMID: 15950528. 12: Plankensteiner K, Reiner H, Rode BM. Catalytic effects of glycine on prebiotic divaline and diproline formation. Peptides. 2005 Jul;26(7):1109-12. doi: 10.1016/j.peptides.2005.01.007. Epub 2005 Feb 16. PMID: 15949627. 13: Kogiso M, Okada Y, Yase K, Shimizu T. Metal-complexed nanofiber formation in water from dicarboxylic valylvaline bolaamphiphiles. J Colloid Interface Sci. 2004 May 15;273(2):394-9. doi: 10.1016/j.jcis.2004.01.062. PMID: 15082373. 14: Chung DM, Nowick JS. Enantioselective molecular recognition between beta- sheets. J Am Chem Soc. 2004 Mar 17;126(10):3062-3. doi: 10.1021/ja031632z. PMID: 15012131. 15: Cárdenas AE, Elber R. Atomically detailed simulations of helix formation with the stochastic difference equation. Biophys J. 2003 Nov;85(5):2919-39. doi: 10.1016/S0006-3495(03)74713-4. PMID: 14581195; PMCID: PMC1303571. 16: Takahashi N, Sato T. Preferential utilization of dipeptides by Porphyromonas gingivalis. J Dent Res. 2001 May;80(5):1425-9. doi: 10.1177/00220345010800050801. PMID: 11437213. 17: Kogiso M, Okada Y, Hanada T, Yase K, Shimizu T. Self-assembled peptide fibers from valylvaline bola-amphiphiles by a parallel beta-sheet network. Biochim Biophys Acta. 2000 Jul 26;1475(3):346-52. doi: 10.1016/s0304-4165(00)00088-x. PMID: 10913835. 18: Li J, Tamura K, Lee CP, Smith PL, Borchardt RT, Hidalgo IJ. Structure- affinity relationships of Val-Val and Val-Val-Val stereoisomers with the apical oligopeptide transporter in human intestinal Caco-2 cells. J Drug Target. 1998;5(5):317-27. doi: 10.3109/10611869808997860. PMID: 9771614. 19: Tamura K, Bhatnagar PK, Takata JS, Lee CP, Smith PL, Borchardt RT. Metabolism, uptake, and transepithelial transport of the diastereomers of Val- Val in the human intestinal cell line, Caco-2. Pharm Res. 1996 Aug;13(8):1213-8. doi: 10.1023/a:1016068421243. PMID: 8865315. 20: Thwaites DT, Hirst BH, Simmons NL. Direct assessment of dipeptide/H+ symport in intact human intestinal (Caco-2) epithelium: a novel method utilising continuous intracellular pH measurement. Biochem Biophys Res Commun. 1993 Jul 15;194(1):432-8. doi: 10.1006/bbrc.1993.1838. PMID: 8333858.