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56480

Sigma-Aldrich

N-Hydroxysuccinimide

≥97.0% (T), for peptide synthesis

Synonym(s):

1-Hydroxy-2,5-pyrrolidinedione, HOSu, NHS

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About This Item

Empirical Formula (Hill Notation):
C4H5NO3
CAS Number:
6066-82-6
Molecular Weight:
115.09
Beilstein/REAXYS Number:
113913
EC Number:
228-001-3
MDL number:
MFCD00005516
UNSPSC Code:
12352005
PubChem Substance ID:
329758217
NACRES:
NA.22

product name

N-Hydroxysuccinimide, purum, ≥97.0% (T)

grade

purum

Quality Level

200

assay

≥97.0% (T)

form

solid

reaction suitability

reaction type: Addition Reactions

mp

95-98 °C (lit.)
95-98 °C

application(s)

peptide synthesis

functional group

imide

SMILES string

ON1C(=O)CCC1=O

InChI

1S/C4H5NO3/c6-3-1-2-4(7)5(3)8/h8H,1-2H2

InChI key

NQTADLQHYWFPDB-UHFFFAOYSA-N

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Application

N-Hydroxysuccinimide (NHS) can be used in the following applications:
  • To synthesize N-succinimidyl 3-(2-pyridyldithio)-propionate, a heterobifunctional reagent useful for protein-protein conjugation and also to incorporate aliphatic thiols into proteins.
  • To synthesize NHS esters of long-chain fatty acids.
  • NHS can activate the phosphonic acid monolayers immobilized on titanium surface for binding with proteins.

Other Notes

may contain 1-3% succinic acid and/or succinic anhydride

pictograms

Corrosion
GHS05

signalword

Danger

hcodes

H315,H318

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
WXBF0366V
WXBC9742V
WXBD9875V
WXBF1260V
WXBD7261V

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Protein thiolation and reversible protein-protein conjugation. N-Succinimidyl 3-(2-pyridyldithio) propionate, a new heterobifunctional reagent.
Carlsson J
The Biochemical Journal, 173(3), 723-723 (1978)
Kengo Nishi et al.
The Journal of chemical physics, 137(22), 224903-224903 (2012-12-20)
We investigated the relationship between the elastic modulus, G and the reaction probability, p for polymer networks. First, we pointed out that the elastic modulus is expressed by G = {(fp∕2 - 1) + O((p - 1)(2))} Nk(B)T∕V (percolated network
Synthesis of long-chain fatty acyl-CoA thioesters using N-hydroxysuccinimide esters.
Blecher M
Methods in Enzymology, 72, 404-408 (1981)
Phosphonic acid monolayers for binding of bioactive molecules to titanium surfaces.
Adden N
Langmuir, 22(19), 8197-8204 (2006)
Burcu Ayoglu et al.
EMBO molecular medicine, 6(7), 918-936 (2014-06-13)
Despite the recent progress in the broad-scaled analysis of proteins in body fluids, there is still a lack in protein profiling approaches for biomarkers of rare diseases. Scarcity of samples is the main obstacle hindering attempts to apply discovery driven
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