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Pierce™ SATA (N-succinimidyl S-acetylthioacetate) (Thermo Scientific™)

Thermo Scientific Pierce SATA is a short-chain (2.8 angstrom spacer arm) reagent for covalent modification of primary amines and addition of a protected yet exposable sulfhydryl group, enabling heterobifunctional crosslinking strategies.

Features of SATA:

• Adds a protected sulfhydryl that can be deprotected by hydroxylamine
• Allows long-term storage of the sulfhydryl-modified molecule
• Forms cleavable disulfide bonds with other sulfhydryl-containing molecules
• Reacts with primary amines (e.g., lysine residues proteins) to form stable amide bonds
• Preserves protein activity with its mild, non-denaturing reaction conditions

SATA (N-succinimidyl S-acetylthioacetate) adds sulfhydryl groups to proteins and other amine-containing molecules in a protected form. The modified molecule can be stored indefinitely and treated with hydroxylamine to expose the labile sulfhydryl group when needed for conjugation reactions. SATA contains an N-hydroxysuccinimide (NHS) ester, which forms a stable, covalent amide bond with primary amines (i.e., lysine residues and the amino termini of proteins) and releases NHS as a by-product. De-protection (deacylation) to generate a free sulfhydryl is accomplished using hydroxylamine-HCl.

Sulfhydryl groups present on proteins, peptides and other compounds are important in protein chemistry/modification reactions. Frequently, thiols are unavailable or absent within the molecules of interest. Several reagents and techniques are available for introducing sulfhydryl groups or disulfides into proteins and peptides, including Traut's Reagent, variants of SPDP, and variants of SATA.

Related Products
Pierce™ Sulfhydryl Addition Kit
Pierce™ SATP
Pierce™ SAT(PEG)4

Pierce™ Sulfhydryl Addition Kit (Thermo Scientific™)

The Thermo Scientific Pierce Sulfhydryl Addition Kit contains all necessary components to introduce free sulfhydryl groups into any primary amine-containing molecule, purify the modified molecule and quantify the added sulfhydryl groups. SATA is a short-chain (2.8 angstrom spacer arm) reagent for covalent modification of primary amines and addition of a protected yet exposable sulfhydryl group, enabling heterobifunctional crosslinking strategies.

Features of SATA:

• Adds a protected sulfhydryl that can be deprotected by hydroxylamine
• Allows long-term storage of the sulfhydryl-modified molecule
• Forms cleavable disulfide bonds with other sulfhydryl-containing molecules
• Reacts with primary amines (e.g., lysine residues proteins) to form stable amide bonds
• Preserves protein activity with its mild, non-denaturing reaction conditions

SATA (N-succinimidyl S-acetylthioacetate) adds sulfhydryl groups to proteins and other amine-containing molecules in a protected form. The modified molecule can be stored indefinitely and treated with hydroxylamine to expose the labile sulfhydryl group when needed for conjugation reactions. SATA contains an N-hydroxysuccinimide (NHS) ester, which forms a stable, covalent amide bond with primary amines (i.e., lysine residues and the amino termini of proteins) and releases NHS as a by-product. De-protection (deacylation) to generate a free sulfhydryl is accomplished using hydroxylamine-HCl.

Sulfhydryl groups present on proteins, peptides and other compounds are important in protein chemistry/modification reactions. Frequently, thiols are unavailable or absent within the molecules of interest. Several reagents and techniques are available for introducing sulfhydryl groups or disulfides into proteins and peptides, including Traut's Reagent, variants of SPDP, and variants of SATA.

Related Products
Pierce™ SATA (N-succinimidyl S-acetylthioacetate)
Pierce™ SATP
Pierce™ SAT(PEG)4

Pierce™ Iodoacetic Acid (Thermo Scientific™)

Thermo Scientific Pierce Iodoacetic Acid (IAA) can react with several protein functional groups but is typically used for specific S-carboxymethylation of sulfhydryls (reduced cysteines).

Features of Pierce Iodocetic Acid (IAA):

• React at slightly alkaline pH for specific S-carboxymethylation of free sulfhydryls
• React at low pH for specific carboxymethylation of methionines
• React at high pH to favor carboxymethylation of histidines and lysines
• Methylate reduced cysteine peptide fragments in protease digests for mass spectrometry

Iodoacetic acid reacts with sulfhydryls on cysteines, imidazolyl side chain nitrogens of histidines, the thioether of methionine and the primary amine group of lysines.The rate of reaction and specificity is dependent on the ionization level, which can be manipulated by the pH of the reaction condition.

Related Products
Pierce™ Iodoacetamide, Single-Use

Pierce™ Traut's Reagent (2-iminothiolane) (Thermo Scientific™)

Thermo Scientific Pierce Traut's Reagent (2-iminothiolane) is a small thiolation compound that reacts with primary amines (e.g., lysine side chains) to add a small spacer arm (8.1 angstroms) terminated by a free sulfhydryl group.

Features of Thermo Scientific Pierce Traut's Reagent (2-iminothiolane):

Simple—one-step conversion of amines to sulfhydryls
Specific—selective and spontaneous modification of primary amines at pH 7-10
• Preserves positive charge to maintain protein solubility

Traut's Reagent (2-iminothiolane or 2-IT) is a cyclic thioimidate compound for thiolation (sulfhydryl addition). Traut's Reagent reacts with primary amines (—NH2) to introduce sulfhydryl (—SH) groups while maintaining charge properties similar to the original amino group. Once added, sulfhydryl groups can be specifically targeted for reaction in a variety of useful labeling, crosslinking and immobilization procedures.

Flexible—incorporates a five-atom spacer arm to reduce steric hindrance
Soluble—preserves the original positive charge to preserve protein solubility

Related Products
Pierce™ SATA

Pierce™ Chloroacetamide, No-Weigh™ Format (Thermo Scientific™)

Thermo Scientific Pierce Chloroacetamide is a sulfhydryl-reactive alkylating reagent used to block reduced cysteine residues for protein characterization. Alkylation with chloroacetamide after cysteine reduction results in the covalent addition of a carbamidomethyl group (57.07 Da) and prevents the formation of disulfide bonds. Reducing agents added after alkylation will react with excess chloroacetamide.

The No-Weigh format, where small amounts of reagent are pre-weighed and packaged separately, prevents the contamination and loss of reagent reactivity over time associated with repetitive opening and closing of a single vial. The format enables use of a fresh vial of reagent each time and eliminates the hassle of weighing out small amounts of reagent.

Related products
Bond-Breaker TCEP Solution, Neutral pH
Pierce Iodoacetic Acid

Pierce™ Citraconic Anhydride (Thermo Scientific™)

Thermo Scientific Pierce Citraconic Anhydride reacts with primary amines to to form an amide bond with a terminal carboxyl group. This modification can be reversed using acidic conditions (pH 3-4) or with hydroxylamine.

Citraconic Anhydride (2-methylmaleic anhydride) is used to block primary amine groups at alkaline pH values (pH 7-9). At acidic pH (3-4), the amide linkage is hydrolyzed and citraconic acid is released, revealing the original amine.

Features of Citraconic Anhydride:

• Temporarily block amines to derivatize other parts of the molecule
• Unblock amines using acidic conditions or hydroxylamine

Pierce™ MMTS (methyl methanethiosulfonate) (Thermo Scientific™)

Thermo Scientific Pierce MMTS (methyl methanethiosulfonate) is a small compound that reversibly blocks cysteines and other sulfhydryl groups, enabling the study of enzyme activation and other protein functions.

Features of MMTS (methyl methanethiosulfonate):

• Converts sulfhydryl groups on cysteine side chains into -S-S-CH3
• Reaction is reversible with DTT or TCEP, restoring the free sulfhydryl
• Used to modify thiol groups in creatine kinase

MMTS (methyl methanethiosulfonate) is a sulfhydryl-reactive compound that can reversibly sulfenylate thiol-containing molecules. Reacting MMTS with reduced sulfhydryls (-SH) results in their modification to dithiomethane (-S-S-CH3). Treatment with reducing agents, such as dithiothreitol (DTT), 2-mercaptoethanol (2-ME) or Tris(2-carboxyethyl) phosphine hydrochloride (TCEP), will cleave the disulfide groups to restore the original sulfhydryl. MMTS is commonly used to study biochemical pathways involving thiol-dependent enzymes.

More Product Data
Specific labeling, enrichment and quantitation of S-nitrosylated peptides using iodoTMT reagents

Related Products
Pierce™ NEM (N-ethylmaleimide)

Pierce™ SATP (N-succinimidyl-S-acetylthiopropionate) (Thermo Scientific™)

Thermo Scientific Pierce SATP is a long-chain (4.1 angstrom spacer arm) reagent for covalent modification of primary amines and addition of a protected yet exposable sulfhydryl group, enabling heterobifunctional crosslinking strategies.

Features of SATP:

• Adds a protected sulfhydryl that can be deprotected by hydroxylamine
• Allows long-term storage of the sulfhydryl-modified molecule
• Offers more steric freedom than SATA for the unmasked sulfhydryl group
• Forms cleavable disulfide bonds with other sulfhydryl-containing molecules
• Reacts with primary amines (e.g., lysine residues proteins) to form stable amide bonds
• Preserves protein activity with its mild, non-denaturing reaction cdonditions

SATP (N-succinimidyl-S-acetylthiopropionate) adds sulfhydryl groups to proteins and other amine-containing molecules in a protected form. The modified molecule can be stored indefinitely and treated with hydroxylamine to expose the labile sulfhydryl group when needed for conjugation reactions. SATP contains an N-hydroxysuccinimide (NHS) ester, which forms a stable, covalent amide bond with primary amines (i.e., lysine residues and the amino termini of proteins) and releases NHS as a by-product. De-protection (deacylation) to generate a free sulfhydryl is accomplished using hydroxylamine-HCl.

Sulfhydryl groups present on proteins, peptides and other compounds are important in protein chemistry/modification reactions. Frequently, thiols are unavailable or absent within the molecules of interest. Several reagents and techniques are available for introducing sulfhydryl groups or disulfides into proteins and peptides, including Traut's Reagent, variants of SPDP, and variants of SATA (e.g., SATP).

Related Products
Pierce™ SATA

Pierce™ Sodium meta-Periodate (Thermo Scientific™)

Thermo Scientific Pierce Sodium meta-Periodate is a gentle oxidizing agent that cleaves cis-diols in carbohydrate sugars to create amine-reactive aldehydes, providing many uses relating to the study and detection of glycoproteins.

Features of Sodium meta-Periodate:

• Convert sugars in sialic acid and other glycosylation groups to reactive aldehydes
Immobilize glycoproteins to a hydrazide-activated solid support
• Conjugate antibodies to glycoprotein enzymes, such as horseradish peroxidase
• Probe for cell-surface polysaccharides
• Detect carbohydrate-containing proteins using hydrazide-containing probes

Sodium meta-periodate converts cis-glycol groups in carbohydrates to amine-reactive aldehyde groups. Carbohydrate groups in glycoproteins are excellent sites for modification or crosslinking reactions because they allow the conjugation reaction to be directed away from amino acids in the polypeptide chain that could be critical for protein activity. Sodium meta-periodate cleaves bonds between adjacent carbon atoms that contain hydroxyl groups (cis-glycols), creating two aldehyde groups that are spontaneously reactive to amine- and hydrazide-activated labeling, immobilization supports and crosslinking reagents.

Pierce™ EMCA (N-ε-maleimidocaproic acid) (Thermo Scientific™)

Thermo Scientific Pierce EMCA is a carboxylic acid compound with a terminal maleimide group that can modify proteins and other molecules by EDC-mediated and sulfhydryl-targeted conjugation.

Features EMCA:

• Convert sulfhydryl groups to carboxyl groups for conjugation to amines via carbodiimide (EDC)
• Prepare maleimide-activated proteins using EDC to modify primary amines
Maleimides react with—SH groups at pH 6.5-7.5, forming stable thioether linkages

EMCA (N-epsilon-maleimidocaproic acid) is a heterobifunctional crosslinker that reacts with sulfhydryl groups to present a terminal carboxyl group. Additionally, the carboxyl can be coupled to amine-containing molecules using the water-soluble carbodiimide EDC. The EDC reaction results in an intermediate ester, which can react with primary amines to form amide bonds. Thus, amine-containing molecules can be modified to contain sulfhydryl-reactive maleimides.

Pierce™ Sulfo-NHS-Acetate (Thermo Scientific™)

Thermo Scientific Pierce Sulfo-NHS-Acetate is a small compound used for blocking primary amines (e.g., lysine side chains). This compound forms stable, covalent amide bonds with amine groups to prevent specific interactions or conjugations.

Sulfo-NHS-Acetate is typically used to prevent polymerization when performing protein crosslinking reactions and when conjugating peptides to carrier proteins for immunogen production. Blocking amines on the peptide allows directed conjugation of carboxylic acids on the peptide to primary amines on the protein using EDC.

Features of Sulfo-NHS-Acetate:

• Irreversibly block primary amines
• Perform reactions in standard non-amine-containing buffers at pH 7 or greater
• Prevent polymerization when performing protein crosslinking reactions

GlycoLink™ Coupling Catalyst (Thermo Scientific™)

The Thermo Scientific GlycoLink Coupling Catalyst decreases reaction times and increases aldehyde-hydrazide coupling efficiency, resulting in greater than 90% coupling of glycoproteins in 4 hours.

Features of the GlycoLink Coupling Catalyst:

Optimized—catalyzes aldehyde-hydrazide and aldehyde-alkoxyamine conjugation reaction
Efficient—maximizes coupling efficiency and decreases required coupling reaction incubation time
Gentle—does not interfere with protein function and is easily removed by desalting or dialysis

The GlycoLink Coupling Catalyst is a two component kit composed of aniline and sodium acetate buffer. The catalyst accelerates the coupling rate of hydrazide and alkoxyamine moieties with reactive aldehydes that have been generated by periodate-oxidation of cis-diols in glycoproteins. The GlycoLink Coupling Catalyst increases the coupling efficiency of these reactions, decreasing the molar excess amounts of labeling reagents that are required for conjugation reactions. The catalyst is also useful for increasing the binding efficiency of oxidized glycoproteins or other carbohydrate-containing molecules to hydrazide resins.

Applications
• Labeling aldehyde-containing molecules with alkoxyamine-biotins
• Labeling aldehyde-containing molecules with hydrazide-biotins
• Increase coupling efficiency of aldehyde-containing molecules to hydrazide resin

Producing reactive aldehydes via sodium meta-periodate oxidation of cis-diols in glycoproteins is a useful technique for variety of protein labeling and detection methods. The GlycoLink Coupling Catalyst (aniline) increases the efficiency of these reactions by acting as a nucleophilic catalyst that accelerates bond formation through a Schiff base intermediate. The catalyst also reduces the amount (molar excess) of hydrazide or alkoxyamine required in labeling reactions, thereby eliminating the need for DMSO to solubilize high concentrations of labeling reagent.

More Product Data
Improved immobilization and conjugation of glycoproteins

Pierce™ Iodoacetamide, Single-Use (Thermo Scientific™)

Thermo Scientific Pierce Iodoacetamide is a sulfhydryl-reactive alkylating reagent used to block reduced cysteine residues for protein characterization and peptide mapping. Alkylation with iodoacetamide after cystine reduction results in the covalent addition of a carbamidomethyl group (57.07 Da) and prevents the formation of disulfide bonds. Reducing agents added after alkylation will react with excess iodoacetamide.

Related Products
Pierce™ Iodoacetic Acid

Pierce™ SAT(PEG)4 (PEGylated N-succinimidyl S-acetylthioacetate) (Thermo Scientific™)

Thermo Scientific Pierce SAT(PEG)4 is a long-arm (18.2 angstroms), pegylated form of SATA, a sulfhydryl-addition reagent for covalent modification of primary amines to facilitate controlled, heterobifunctional crosslinking.

Features of SAT(PEG)4:

• Thiolate and PEGylate primary amines in one step
• Add sulfhydryl groups for heterobifunctional crosslinking without compromising protein solubility
• NHS-activated for efficient PEGylation of primary amines at pH 7-9; reaction of NHS-ester group results in formation of stable, irreversible amide bonds
• Pure compound with defined structure and molecular weight, ensuring reproducible protein-modification effects
• PEG spacer provides unique advantages, including increased stability, reduced tendency toward aggregation and reduced immunogenicity

SAT(PEG)4 is the abbreviation for N-Succinimidyl S-acetyl(thiotetraethylene glycol), an amine-reactive reagent for PEGylating and adding sulfhydryl groups to proteins and other amine-containing molecules. Like SATA and other S-acetyl (SAT) reagents, SAT(PEG)4 is most frequently used in bioconjugation methods to incorporate sulfhydryl (—SH) groups into proteins as part of a two-step or heterobifunctional crosslinking strategy. The SAT group prevents oxidation of the sulfur atom but is easily removed by treatment with hydroxylamine when the unprotected sulfhydryl group is needed for conjugation. The polyethylene glycol (PEG) spacer arm in SAT(PEG)4 minimizes steric hindrance and provides added solubility to the modified and conjugated molecules.

Specific reactivity to primary amines (e.g., lysine residues in proteins) occurs via the NHS-ester group. Spontaneous reaction in phosphate or other non-amine buffer at pH 7-9 results in formation of stable, covalent, amide bonds. Upon deprotection of the sulfhydryl group with hydroxylamine, molecules that have been modified with SAT(PEG)4 can be reacted with other proteins or surfaces that have been maleimide-activated with heterobifunctional crosslinkers like Sulfo-SMCC or SM(PEG)n Reagents.

Related Products
Pierce™ SATA

Pierce™ Hydroxylamine-HCl (Thermo Scientific™)

Thermo Scientific Pierce Hydroxylamine-HCl has many uses, which include cleaving Asn-Gly peptide bonds and deprotecting (exposing) sulfhydryls on SATA-modified molecules for conjugation.

Features of Hydroxylamine-HCl:

• Quench amine-labeling or crosslinking reactions (e.g., with NHS esters)
• Expose protected sulfhydryl groups on SATA-modified molecules
• Cleave carbonyl-containing crosslinkers such as EGS and Sulfo-EGS

Hydroxylamine·HCl is a strong reducing agent that is useful in biochemical crosslinking applications, including the deacetylation of SATA and chemical cleavage of EGS and Sulfo-EGS. Hydroxylamine converts carbonyl compounds (aldehydes and ketones) to their oxime derivatives in the presence of a weak base. Therefore, crosslinkers and other compounds that contain a carbonyl within their structure are cleavable with hydroxylamine·HCl.

Pierce™ AEDP (3-[(2-aminoethyl)dithio]propionic acid) (Thermo Scientific™)

Thermo Scientific Pierce AEDP is an amine-and-carboxyl compound with an internal disulfide bond. AEDP enables construction, extension and modification of several functional groups on proteins and surfaces.

Features of AEDP:

• Use as a spacer arm in conjugation schemes
• Use for reversible immobilization applications
• Cleave the internal disulfide bond with reducing agents
• Incorporate amine or carboxyl groups into proteins/peptides using crosslinking agents
• React the amine end with amine-reactive acylation agents
• Use with water-soluble carbodiimide (EDC) to conjugate to amines or carboxylates

AEDP (3-[(2-aminoethyl)dithio]propionic acid·HCl) is a cleavable amino acid that can be reacted with amine-reactive acylation agents to create amide bonds. Alternatively, the carbodiimide EDC can be used to conjugate AEDP to molecules containing amines or carboxylates, which results in some degree of polymerization. Reducing agents, such as DTT and TCEP, are effective for cleaving the disulfide bond.

Pierce™ NEM (N-ethylmaleimide) (Thermo Scientific™)

Thermo Scientific Pierce N-Ethylmaleimide (NEM) is a small compound that forms stable, covalent thioether bonds with sulfhydryls (e.g., reduced cysteines), enabling them to be permanently blocked to prevent disulfide bond formation.

Features of N-Ethylmaleimide (NEM):

• Permanently block sulfhydryls to prevent disulfide bond formation.
• Monitor the reaction by measuring the decrease in absorbance at 300nm
• Block sulfhydryl-containing reagents that interfere in enzyme assays

N-Ethylmaleimide (NEM) is an alkylating reagent that reacts with sulfhydryls. At pH 6.5-7.5, the maleimide reaction is specific for sulfhdryls; however, at pH values greater than 7.5, reactivity with amino groups occurs. Maleimide groups react with sulfhydryls by nucleophilic attack of the thiolate anion on one of the carbons of the double bond. When sufficient sulfhydryls have been blocked, the reaction can be monitored by measuring the decrease in absorbance at 300nm as the double bond becomes a single bond. The resulting thioether group is non-reversible and terminates in an ethyl group, blocking or capping the sulfhydryl.

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Pierce™ MMTS (methyl methanethiosulfonate)

Pierce™ APTS (3-aminopropyltriethoxysilane) (Thermo Scientific™)

Thermo Scientific Pierce APTS (3-aminopropyltriethoxysilane) is a silylation reagent for coating glass and silica surfaces to add primary amines, which can be used to crosslink and immobilize proteins and other molecules.

Features of 3-Aminopropyltriethoxysilane:

• Crosslinking agents such as BS3, EDC and Sulfo-SMCC can be used to immobilize proteins, peptides, modified DNA, etc., to the treated surface
• Coats certain plastic surfaces noncovalently to create a reactive film
• Chemically adheres tissue sections to glass slides for immunohistochemistry

3-Aminopropyltriethoxysilane (APTS) is a surface treatment used to chemically couple various ligands to glass or silica surfaces such as glass slides. 3-aminopropyltriethoxysilane is first coupled to glass or silica through the silane. Compounds of interest are then coupled to the newly added amino groups directly, or additional chemistries are applied using the amino function prior to coupling.