Cysteinesulfenic acid | CAS#73243-12-6 | protein-sulfenic acid

MedKoo Cat#: 597026 | Name: Cysteinesulfenic acid

Description:

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

Cysteine sulfenic acid is an intermediate in disulfide bond formation and nonenzymatic protein folding. As a posttranslational protein modification, cysteine sulfenic acid (Cys-SOH) is well established as an oxidative stress-induced mediator of enzyme function and redox signaling. Cys-SOH is also shown to play a role in spontaneous disulfide-based dimerization of peptide molecules containing free cysteine residues. In total, the data presented expose a chemically ubiquitous role for Cys-SOH in solutions of free cysteine-containing protein exposed to air.

Chemical Structure

Cysteinesulfenic acid

CAS#73243-12-6

Theoretical Analysis

MedKoo Cat#: 597026

Name: Cysteinesulfenic acid

CAS#: 73243-12-6

Chemical Formula: C3H7NO3S

Exact Mass: 137.0147

Molecular Weight: 137.15

Elemental Analysis: C, 26.27; H, 5.14; N, 10.21; O, 35.00; S, 23.38

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.

Bulk Inquiry

Related CAS #

No Data

Synonym

Cysteinesulfenic acid; L-Cysteinesulfenic acid; 3-Sulfeno-L-alanine; L-Cysteine sulfoxide; L-Cysteine sulfenic acid;

IUPAC/Chemical Name

(2R)-2-Amino-3-(hydroxysulfanyl)propanoic acid

InChi Key

FXIRVRPOOYSARH-REOHCLBHSA-N

InChi Code

InChI=1S/C3H7NO3S/c4-2(1-8-7)3(5)6/h2,7H,1,4H2,(H,5,6)/t2-/m0/s1

SMILES Code

O=C(O)[C@@H](N)CSO

Appearance

Solid powder

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

Soluble in DMSO

Shelf Life

>2 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

2934.99.9001

More Info

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	Soluble in DMSO	0.0	100.00

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 137.15 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

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RegB kinase activity is repressed by oxidative formation of cysteine sulfenic acid. J Biol Chem. 2013 Feb 15;288(7):4755-62. doi: 10.1074/jbc.M112.413492. Epub 2013 Jan 10. PMID: 23306201; PMCID: PMC3576080. 13: Crump KE, Juneau DG, Poole LB, Haas KM, Grayson JM. The reversible formation of cysteine sulfenic acid promotes B-cell activation and proliferation. Eur J Immunol. 2012 Aug;42(8):2152-64. doi: 10.1002/eji.201142289. PMID: 22674013; PMCID: PMC3659792. 14: Qian J, Wani R, Klomsiri C, Poole LB, Tsang AW, Furdui CM. A simple and effective strategy for labeling cysteine sulfenic acid in proteins by utilization of β-ketoesters as cleavable probes. Chem Commun (Camb). 2012 Apr 28;48(34):4091-3. doi: 10.1039/c2cc17868k. Epub 2012 Mar 20. PMID: 22430672; PMCID: PMC3568515. 15: Kaplan N, Urao N, Furuta E, Kim SJ, Razvi M, Nakamura Y, McKinney RD, Poole LB, Fukai T, Ushio-Fukai M. Localized cysteine sulfenic acid formation by vascular endothelial growth factor: role in endothelial cell migration and angiogenesis. Free Radic Res. 2011 Oct;45(10):1124-35. doi: 10.3109/10715762.2011.602073. Epub 2011 Jul 25. PMID: 21740309; PMCID: PMC3685280. 16: Rehder DS, Borges CR. Cysteine sulfenic acid as an intermediate in disulfide bond formation and nonenzymatic protein folding. Biochemistry. 2010 Sep 7;49(35):7748-55. doi: 10.1021/bi1008694. PMID: 20712299; PMCID: PMC2945302. 17: Rehder DS, Borges CR. Possibilities and pitfalls in quantifying the extent of cysteine sulfenic acid modification of specific proteins within complex biofluids. BMC Biochem. 2010 Jul 1;11:25. doi: 10.1186/1471-2091-11-25. PMID: 20594348; PMCID: PMC2916888. 18: Heinecke J, Ford PC. Formation of cysteine sulfenic acid by oxygen atom transfer from nitrite. J Am Chem Soc. 2010 Jul 14;132(27):9240-3. doi: 10.1021/ja102221e. PMID: 20565124. 19: Regazzoni L, Panusa A, Yeum KJ, Carini M, Aldini G. 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