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56480

Sigma-Aldrich

N-Hydroxysuccinimide

purum, ≥97.0% (T)

Synonym(s):
NHS, 1-Hydroxy-2,5-pyrrolidinedione, HOSu
Empirical Formula (Hill Notation):
C4H5NO3
CAS Number:
Molecular Weight:
115.09
Beilstein:
113913
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.22

Quality Level

grade

purum

assay

≥97.0% (T)

reaction suitability

reaction type: Addition Reactions

mp

95-98 °C (lit.)
95-98 °C

application(s)

peptide synthesis

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.

Packaging

25, 100 g in poly bottle
1 kg in poly bottle

Other Notes

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

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

Certificate of Analysis

Certificate of Origin

More documents

Quotes and Ordering

Synthesis of long-chain fatty acyl-CoA thioesters using N-hydroxysuccinimide esters.
Blecher M
Methods in Enzymology, 72, 404-408 (1981)
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
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
Phosphonic acid monolayers for binding of bioactive molecules to titanium surfaces.
Adden N
Langmuir, 22(19), 8197-8204 (2006)

Articles

Coupling Reagents

In principle, the seemingly simple formation of a peptide bond can be accomplished using all the procedures available in organic chemistry for the synthesis of carboxylic acid amides. However, due to the presence of various functional groups in natural and unnatural amino acids and particularly the requirement for full retention of chiral integrity, the coupling of amino acids and peptides under mild conditions can be challenging. A plethora of coupling reagents has been developed superseding each other in efficiency and suitability for specific applications (e.g., solid-phase peptide synthesis or fragment condensation).

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