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Sigma-Aldrich

N-Hydroxysulfosuccinimide sodium salt

≥98% (HPLC), for peptide synthesis

Synonym(s):

Hydroxy-2,5-dioxopyrrolidine-3-sulfonicacid sodium salt, Sulfo-NHS

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About This Item

Empirical Formula (Hill Notation):
C4H4NNaO6S
CAS Number:
106627-54-7
Molecular Weight:
217.13
Beilstein:
6359129
MDL number:
MFCD00043100
UNSPSC Code:
12352005
PubChem Substance ID:
57651582
NACRES:
NA.22

product name

N-Hydroxysulfosuccinimide sodium salt, ≥98% (HPLC)

Assay

≥98% (HPLC)

form

powder

composition

carbon, 21.57-22.68 (anhydrous)
nitrogen, 6.28-6.61 (anhydrous)

reaction suitability

reaction type: Addition Reactions

impurities

≤4% water

application(s)

peptide synthesis

SMILES string

[Na+].ON1C(=O)CC(C1=O)S([O-])(=O)=O

InChI

1S/C4H5NO6S.Na/c6-3-1-2(12(9,10)11)4(7)5(3)8;/h2,8H,1H2,(H,9,10,11);/q;+1/p-1

InChI key

RPENMORRBUTCPR-UHFFFAOYSA-M

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Application

N-Hydroxysulfosuccinimide sodium salt is a water-soluble sulfonated analog of N-hydroxysuccinimide. It can undergo a coupling reaction with carboxylic acids in the presence of carbodiimides such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide(EDC) to form hydrophilic N-hydroxysulfosuccinimide active esters. These esters are useful in protein cross-linking experiments.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Sulfo-NHS is used for preparing hydrophilic active esters, e.g. for crosslinking agents

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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N-hydroxysulfosuccinimide active esters: bis (N-hydroxysulfosuccinimide) esters of two dicarboxylic acids are hydrophilic, membrane-impermeant, protein cross-linkers.
Staros JV
Biochemistry, 21(17), 3950-3955 (1982)
Karen S Cheung Tung Shing et al.
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International journal of peptide and protein research, 30(1), 117-124 (1987-07-01)
N-Hydroxysulfosuccinimide esters are reactive functional groups employed in a variety of protein modification reagents, especially cross-linking reagents. For these compounds, hydrolysis is the most important reaction competing for reaction of the esters with nucleophilic groups in proteins. We have employed
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