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56480

Sigma-Aldrich

N-Hydroxysuccinimide

≥97.0% (T), for peptide synthesis

Sinonimo/i:

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

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About This Item

Formula empirica (notazione di Hill):
C4H5NO3
Numero CAS:
Peso molecolare:
115.09
Beilstein:
113913
Numero CE:
Numero MDL:
Codice UNSPSC:
12352005
ID PubChem:
NACRES:
NA.22

product name

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

Grado

purum

Livello qualitativo

Saggio

≥97.0% (T)

Forma fisica

solid

Impiego in reazioni chimiche

reaction type: Addition Reactions

Punto di fusione

95-98 °C (lit.)
95-98 °C

applicazioni

peptide synthesis

Stringa SMILE

ON1C(=O)CCC1=O

InChI

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

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Applicazioni

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.

Altre note

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

Pittogrammi

Corrosion

Avvertenze

Danger

Indicazioni di pericolo

Classi di pericolo

Eye Dam. 1 - Skin Irrit. 2

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

Eyeshields, Gloves, type N95 (US)


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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
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

Articoli

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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