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G3272 Sigma

Guanidine hydrochloride

for molecular biology, ≥99%

Synonym: Aminoformamidine hydrochloride, Aminomethanamidine hydrochloride, Guanidinium chloride

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Description

Application

Strong chaotropic agent useful for the denaturation and subsequent refolding of proteins. This strong denaturant can solubilize insoluble or denatured proteins such as inclusion bodies. This can be used as the first step in refolding proteins or enzymes into their active form. Urea and dithiothreitol (DTT) may also be necessary.

Guanidine hydrochloride is used in RNA isolation to dissociate nucleoproteins and inhibit RNase.

Caution

May agglomerate upon storage. The quality of the product does not appear to be affected and solutions prepared from the free-flowing and lumpy guanidine hydrochloride appear identical.

Preparation Note

In order to make an 8M solution in water, one must heat the solution to 35 °C for approximately 30 minutes.
The maximum solubility of guanidine hydrochloride in water at room temperature is approximately 6M.

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Personal Protective Equipment 
WGK Germany 
1
RTECS 
MF4300000

Protocols & Articles

Protocols

TRI Reagent® Protocol

1A. Tissue: Homogenize tissue samples in TRI Reagent (1 ml per 50–100 mg of tissue) in a Polytron® or other appropriate homogenizer.
Keywords: AGE, Buffers, Cell disruption, Centrifugation, Degradations, Digestions, Electrophoresis, Evaporation, Gel electrophoresis, Homogenization, PAGE, Polymerase chain reaction, Precipitation, Sample preparations, Separation, Solvents, Western blot

Peer-Reviewed Papers

References

Set your institution to view full text papers.

Inclusion bodies and purification of proteins in biologically active forms. Mukhopadhyay, A. Adv. Biochem. Eng. Biotechnol. 56, 61-109., (1997)

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High Level Expression and Refolding of Mouse Interleukin 4 Synthesized in Escherichia coli. Levine, A.D., et al. J. Biol. Chem. 270, 7445-7452, (1995)

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In vitro folding of inclusion body proteins. Rudloph, R. and Lilie, H. FASEB J. 10, 49-56, (1996)

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Solubilization of protein aggregates. Marston, F.A.O. and Hartley, D.L. Meth. Enzymol. 182, 264-276, (1990)

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Recovery of a foreign protein from the periplasm of Escherichia coli by chemical permeabilization. Naglak, T.J. and Wang, H.Y. Enzyme Microb. Technol. 12, 603, (1990)

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Mutations in the nonstructural protein 3A confer resistance to the novel enterovirus replication inhibitor TTP-8307. Armando M. De Palma et al Antimicrob. Agents Chemother. 53, 1850-7, (2009)

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Aminoalkyl derivatives of guanidine diaromatic minor groove binders with antiprotozoal activity. McKeever C, Kaiser M, and Rozas I J. Med. Chem. 56(3), 700-11, (2013)

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Photoclickable dendritic molecular glue: noncovalent-to-covalent photochemical transformation of protein hybrids. Uchida N, Okuro K, Niitani Y, et al. J. Am. Chem. Soc. 135(12), 4684-7, (2013)

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An improved synthesis of (-)-5,11-dideoxytetrodotoxin. Adachi M, Imazu T, Isobe M, et al. J. Org. Chem. 78(4), 1699-705, (2013)

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Improved tumor targeting of anti-HER2 nanobody through N-succinimidyl 4-guanidinomethyl-3-iodobenzoate radiolabeling. Pruszynski M, Koumarianou E, Vaidyanathan G, et al. J. Nucl. Med. 55(4), 650-6, (2014)

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Urea and guanidine hydrochloride denaturation curves. Shirley BA Methods Mol. Biol. 40, 177-90, (1995)

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Modulation of hydrophobic interactions by proximally immobilized ions. Ma CD, Wang C, Acevedo-Vélez C, et al. Nature 517(7534), 347-50, (2015)

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Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species. Denis Fourches et al Chem. Res. Toxicol. 23, 171-83, (2010)

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Rapid detection of economic adulterants in fresh milk by liquid chromatography-tandem mass spectrometry. Abernethy G and Higgs K J. Chromatogr. A 1288, 10-20, (2013)

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Separation performance of guanidinium-based ionic liquids as stationary phases for gas chromatography. Qiao L, Lu K, Qi M, et al. J. Chromatogr. A 1276, 112-9, (2013)

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The effect of guanidinylation of PEGylated poly(2-aminoethyl methacrylate) on the systemic delivery of siRNA. Cheng Q, Huang Y, Zheng H, et al. Biomaterials 34(12), 3120-31, (2013)

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Kinetic evidence for a two-stage mechanism of protein denaturation by guanidinium chloride. Jha SK and Marqusee S Proc. Natl. Acad. Sci. U. S. A. 111(13), 4856-61, (2014)

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Visual detection of arginine based on the unique guanidino group-induced aggregation of gold nanoparticles. Pu W, Zhao H, Huang C, et al. Anal. Chim. Acta 764, 78-83, (2013)

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Partitioning of superoxide and hydrogen peroxide production by mitochondrial respiratory complex I. Grivennikova VG and Vinogradov AD Biochim. Biophys. Acta 1827(3), 446-54, (2013)

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Structure-property relationships of energetic nitrogen-rich salts composed of triaminoguanidinium or ammonium cation and tetrazole-based anions. Shao Y, Zhu W, and Xiao H J. Mol. Graph. Model. 40, 54-63, (2013)

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Denaturation-resistant bifunctional colloidal superstructures assembled via the proteinaceous barnase-barstar interface. Aghayeva UF, Nikitin MP, Lukash SV, et al. ACS Nano 7(2), 950-61, (2013)

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Guanidino groups greatly enhance the action of antimicrobial peptidomimetics against bacterial cytoplasmic membranes. Andreev K, Bianchi C, Laursen JS, et al. Biochim. Biophys. Acta 1838(10), 2492-502, (2014)

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Synthesis of highly substituted oxetanes via [2+2] cycloaddition reactions of allenoates catalyzed by a guanidine Lewis base. Selig P, Turočkin A, and Raven W Chem. Commun. (Camb.) 49(28), 2930-2, (2013)

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Molecular weight distribution analysis by ultracentrifugation: adaptation of a new approach for mucins. Gillis RB, Adams GG, Wolf B, et al. Carbohydr. Polym. 93(1), 178-83, (2013)

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Mechanism of Hsp104/ClpB inhibition by prion curing Guanidinium hydrochloride. Kummer E, Oguchi Y, Seyffer F, et al. FEBS Lett. 587(6), 810-7, (2013)

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A network of genes connects polyglutamine toxicity to ploidy control in yeast. Kaiser CJ, Grötzinger SW, Eckl JM, et al. Nat. Commun. 4, 1571, (2013)

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Guanidine hydrochloride denaturation studies of mutant forms of staphylococcal nuclease. Shortle D J. Cell. Biochem. 30(4), 281-9, (1986)

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The molecular mechanism of Hsp100 chaperone inhibition by the prion curing agent guanidinium chloride. Zeymer C, Werbeck ND, Schlichting I, et al. J. Biol. Chem. 288(10), 7065-76, (2013)

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Comparison of the thermal denaturing of human serum albumin in the presence of guanidine hydrochloride and 1-butyl-3-methylimidazolium ionic liquids. Heller WT J. Phys. Chem. B 117(8), 2378-83, (2013)

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Effect of three trifluoromethanesulfonate ionic liquids on the activity, stability and conformation of laccase. Yu X, Zou F, Li Y, et al. Int. J. Biol. Macromol. 56, 62-8, (2013)

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Thermodynamic effects of the alteration of the axial ligand on the unfolding of thermostable cytochrome C. Behera RK, Nakajima H, Rajbongshi J, et al. Biochemistry 52(8), 1373-84, (2013)

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Stabilization of ferrochelatase via lysine residues on the carboxyl terminal extension. Wong KF and Ho J Protein Pept. Lett. 20(9), 977-81, (2013)

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Pre-existent asymmetry in the human cyclooxygenase-2 sequence homodimer. Dong L, Sharma NP, Jurban BJ, et al. J. Biol. Chem. 288(40), 28641-55, (2013)

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Dual role of acetate as a nucleophile and as an internal base in cycloplatination reaction of sym-N,N',N″-triarylguanidines. Elumalai P, Thirupathi N, and Nethaji M Inorg. Chem. 52(4), 1883-94, (2013)

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A template approach for the characterization of linear polyamines and derivatives in spider venom. Tzouros M, Chesnov S, Bigler L, et al. Eur. J. Mass Spectrom. (Chichester, Eng.) 19(1), 57-69, (2013)

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Role of a guanidinium cation-phosphodianion pair in stabilizing the vinyl carbanion intermediate of orotidine 5'-phosphate decarboxylase-catalyzed reactions. Goryanova B, Goldman LM, Amyes TL, et al. Biochemistry 52(42), 7500-11, (2013)

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Aromatic oligoamide macrocycles with a backbone of reduced constraint. Kline M, Wei X, and Gong B Org. Lett. 15(18), 4762-5, (2013)

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Energetics of the Escherichia coli DnaT protein trimerization reaction. Szymanski MR, Jezewska MJ, and Bujalowski W Biochemistry 52(11), 1858-73, (2013)

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Synthesis of novel phosphorylated guanidine derivatives from cyanamide and their anti-inflammatory activity. Katla VR, Syed R, Kuruva CS, et al. Chem. Pharm. Bull. 61(1), 25-32, (2013)

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Striking stabilization of Rana catesbeiana ribonuclease 3 by guanidine hydrochloride. Solé M, Brandt W, and Arnold U FEBS Lett. 587(6), 737-42, (2013)

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Neighboring effect in fragmentation pathways of cage guanylhydrazones in the gas phase. Šekutor M, Glasovac Z, and Mlinarić-Majerski K J. Phys. Chem. A 117(10), 2242-52, (2013)

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Pharmacophoric features of drugs with guanylurea moiety: an electronic structure analysis. Kasetti Y and Bharatam PV J. Mol. Model. 19(4), 1865-74, (2013)

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Conformational stability and ligand binding properties of BldR, a member of the MarR family, from Sulfolobus solfataricus. Fiorentino G, Del Giudice I, Petraccone L, et al. Biochim. Biophys. Acta 1844(6), 1167-72, (2014)

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A guanidinylated bioreducible polymer as a novel gene carrier to the corpus cavernosum of mice with high-cholesterol diet-induced erectile dysfunction. Ryu JK, Choi MJ, Kim TI, et al. Andrology 1(2), 216-22, (2013)

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Solution and in silico studies on the recombinant lectin from Cicer arietinum seeds. Wakankar MS, Krishnasastry MV, Jaokar TM, et al. Int. J. Biol. Macromol. 56, 149-55, (2013)

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Monanchomycalin C, a new pentacyclic guanidine alkaloid from the far-eastern marine sponge Monanchora pulchra. Tabakmakher KM, Denisenko VA, Guzii AG, et al. Nat. Prod. Commun. 8(10), 1399-402, (2013)

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Structural landscape of the proline-rich domain of Sos1 nucleotide exchange factor. McDonald CB, Bhat V, Kurouski D, et al. Biophys. Chem. 175-176, 54-62, (2013)

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Evidence for a molten globule state in Cicer α-galactosidase induced by pH, temperature, and guanidine hydrochloride. Singh N, Kumar R, Jagannadham MV, et al. Appl. Biochem. Biotechnol. 169(8), 2315-25, (2013)

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At very low concentrations known chaotropes act as kosmotropes for the N and B isoforms of human serum albumin. Sen P, Khan MM, Equbal A, et al. Biochem. Cell Biol. 91(2), 72-8, (2013)

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4(R/S)-Amino/guanidino-substituted proline peptides: design, synthesis and DNA transfection properties. Umashankara M, Nanda M, Sonar M, et al. Chimia 66(12), 936-40, (2012)

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Merck 14,4562

Beil. 3,IV,150

Aldrich MSDS 1, 998:C / Corp MSDS 1 (1), 1803:D / FT-IR 1 (1), 818:A / FT-IR 2 (1), 1388:B / IR-Spectra (3), 485:D / IR-Spectra (2), 429:D / RegBook 1 (1), 961:K / Sax 6, 1488 / Sigma FT-IR 1 (2), 597:C / Sigma FT-IR 1 (2), 597:D / Structure Index 1, 149:C:7

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