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MedKoo Cat#: 146045 | Name: Nopaline

Description:

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

Nopaline is a naturally occurring compound found in the Opuntia species, commonly known as prickly pear cactus. It is primarily known for its potential antioxidant and anti-inflammatory properties, which help reduce oxidative stress and inflammation in the body. Nopaline works by modulating enzymes and signaling pathways involved in inflammatory responses, making it beneficial in managing conditions like arthritis and metabolic syndrome. Additionally, nopaline has been studied for its potential to improve cardiovascular health and support immune system function due to its bioactive compounds.

Chemical Structure

Nopaline
Nopaline
CAS#22350-70-5

Theoretical Analysis

MedKoo Cat#: 146045

Name: Nopaline

CAS#: 22350-70-5

Chemical Formula: C11H20N4O6

Exact Mass: 304.1400

Molecular Weight: 304.30

Elemental Analysis: C, 43.42; H, 6.62; N, 18.41; O, 31.55

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Nopaline;
IUPAC/Chemical Name
((S)-1-carboxy-4-guanidinobutyl)-D-glutamic acid
InChi Key
LMKYZBGVKHTLTN-NKWVEPMBSA-N
InChi Code
1S/C11H20N4O6/c12-11(13)14-5-1-2-6(9(18)19)15-7(10(20)21)3-4-8(16)17/h6-7,15H,1-5H2,(H,16,17)(H,18,19)(H,20,21)(H4,12,13,14)/t6-,7+/m0/s1
SMILES Code
NC(=N)NCCC[C@H](N[C@H](CCC(O)=O)C(O)=O)C(O)=O
Appearance
To be determined
Purity
>98% (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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 304.30 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.

Recalculate based on batch purity %
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
1: Lacroix B, Citovsky V. Nopaline-type Ti plasmid of Agrobacterium encodes a VirF-like functional F-box protein. Sci Rep. 2015 Nov 20;5:16610. doi: 10.1038/srep16610. PMID: 26586289; PMCID: PMC4653730. 2: Cao X, Xia Z, Yan W, He S, Xu X, Wei Z, Ye Y, Zheng H. Colorimetric biosensing of nopaline synthase terminator using Fe3O4@Au and hemin-functionalized reduced graphene oxide. Anal Biochem. 2020 Aug 1;602:113798. doi: 10.1016/j.ab.2020.113798. Epub 2020 Jun 4. PMID: 32505706. 3: Shao S, van Heusden GPH, Hooykaas PJJ. Complete Sequence of Succinamopine Ti- Plasmid pTiEU6 Reveals Its Evolutionary Relatedness with Nopaline-Type Ti- Plasmids. Genome Biol Evol. 2019 Sep 1;11(9):2480-2491. doi: 10.1093/gbe/evz173. PMID: 31386108; PMCID: PMC6733357. 4: Montoya AL, Chilton MD, Gordon MP, Sciaky D, Nester EW. Octopine and nopaline metabolism in Agrobacterium tumefaciens and crown gall tumor cells: role of plasmid genes. J Bacteriol. 1977 Jan;129(1):101-7. doi: 10.1128/jb.129.1.101-107.1977. PMID: 830636; PMCID: PMC234901. 5: An G, Costa MA, Ha SB. Nopaline synthase promoter is wound inducible and auxin inducible. Plant Cell. 1990 Mar;2(3):225-33. doi: 10.1105/tpc.2.3.225. PMID: 2152114; PMCID: PMC159879. 6: Akiyama H, Nakamura F, Yamada C, Nakamura K, Nakajima O, Kawakami H, Harikai N, Furui S, Kitta K, Teshima R. A screening method for the detection of the 35S promoter and the nopaline synthase terminator in genetically modified organisms in a real-time multiplex polymerase chain reaction using high-resolution melting-curve analysis. Biol Pharm Bull. 2009 Nov;32(11):1824-9. doi: 10.1248/bpb.32.1824. PMID: 19881291. 7: Lippincott JA, Beiderbeck R, Lippincott BB. Utilization of octopine and nopaline by Agrobacterium. J Bacteriol. 1973 Oct;116(1):378-83. doi: 10.1128/jb.116.1.378-383.1973. PMID: 4745420; PMCID: PMC246433. 8: Han ZF, Hunter DM, Sibbald S, Zhang JS, Tian L. Biological activity of the tzs gene of nopaline Agrobacterium tumefaciens GV3101 in plant regeneration and genetic transformation. Mol Plant Microbe Interact. 2013 Nov;26(11):1359-65. doi: 10.1094/MPMI-04-13-0106-R. PMID: 24088018. 9: Hattori Y, Iwata K, Suzuki K, Uraji M, Ohta N, Katoh A, Yoshida K. Sequence characterization of the vir region of a nopaline type Ti plasmid, pTi-SAKURA. Genes Genet Syst. 2001 Apr;76(2):121-30. doi: 10.1266/ggs.76.121. PMID: 11434457. 10: Bomhoff G, Klapwijk PM, Kester HC, Schilperoort RA, Hernalsteens JP, Schell J. Octopine and nopaline synthesis and breakdown genetically controlled by a plasmid of Agrobacterium tumefaciens. Mol Gen Genet. 1976 May 7;145(2):177-81. doi: 10.1007/BF00269591. PMID: 934053. 11: Depicker A, Stachel S, Dhaese P, Zambryski P, Goodman HM. Nopaline synthase: transcript mapping and DNA sequence. J Mol Appl Genet. 1982;1(6):561-73. PMID: 7153689. 12: Shaw CH, Carter GH, Watson MD, Shaw CH. A functional map of the nopaline synthase promoter. Nucleic Acids Res. 1984 Oct 25;12(20):7831-46. doi: 10.1093/nar/12.20.7831. PMID: 6493982; PMCID: PMC320203. 13: Marincs F, White DW. Nopaline causes a conformational change in the NocR regulatory protein-nocR promoter complex of Agrobacterium tumefaciens Ti plasmid pTiT37. Mol Gen Genet. 1993 Oct;241(1-2):65-72. doi: 10.1007/BF00280202. PMID: 8232213. 14: Melchers LS, Maroney MJ, den Dulk-Ras A, Thompson DV, van Vuuren HA, Schilperoort RA, Hooykaas PJ. Octopine and nopaline strains of Agrobacterium tumefaciens differ in virulence; molecular characterization of the virF locus. Plant Mol Biol. 1990 Feb;14(2):249-59. doi: 10.1007/BF00018565. PMID: 2101693. 15: Schardl CL, Kado CI. A functional map of the nopaline catabolism genes on the Ti plasmid of Agrobacterium tumefaciens C58. Mol Gen Genet. 1983;191(1):10-6. doi: 10.1007/BF00330882. PMID: 6577260. 16: Gafni Y. Nopaline synthase gene is expressed in Escherichia coli and in cucumber cells under a hybrid promoter. Plant Mol Biol. 1990 Jul;15(1):173-4. doi: 10.1007/BF00017738. PMID: 2103433. 17: Huang D, Qian J, Shi Z, Zhao J, Fang M, Xu Z. CRISPR-Cas12a-Assisted Multicolor Biosensor for Semiquantitative Point-of-Use Testing of the Nopaline Synthase Terminator in Genetically Modified Crops by Unaided Eyes. ACS Synth Biol. 2020 Nov 20;9(11):3114-3123. doi: 10.1021/acssynbio.0c00365. Epub 2020 Oct 13. PMID: 33047952. 18: Otten LA, Schilperoort RA. A rapid micro scale method for the detection of lysopine and nopaline dehydrogenase activities. Biochim Biophys Acta. 1978 Dec 8;527(2):497-500. doi: 10.1016/0005-2744(78)90363-7. PMID: 31918. 19: Kemp JD, Sutton DW, Hack E. Purification and characterization of the crown gall specific enzyme nopaline synthase. Biochemistry. 1979 Aug 21;18(17):3755-60. doi: 10.1021/bi00584a017. PMID: 476084. 20: Palanichelvam K, Veluthambi K. Octopine- and Nopaline-Inducible Proteins in Agrobacterium tumefaciens Are Also Induced by Arginine. Curr Microbiol. 1996 Sep;33(3):156-62. doi: 10.1007/s002849900093. PMID: 8672091.