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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:
Molecular Weight:
115.09
Beilstein:
113913
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

product name

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

grade

purum

Quality Level

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

Signal Word

Danger

Hazard Statements

Hazard Classifications

Eye Dam. 1 - Skin Irrit. 2

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

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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)
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
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

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