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43720

Sigma-Aldrich

N,N′-Disuccinimidyl carbonate

≥95.0% (NMR), for peptide synthesis

Sinonimo/i:

N-Succinimidyl carbonate, DSC, Di(N-succinimidyl) carbonate

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About This Item

Formula empirica (notazione di Hill):
C9H8N2O7
Numero CAS:
74124-79-1
Peso molecolare:
256.17
Beilstein:
1499137
Numero CE:
277-730-3
Numero MDL:
MFCD00009767
Codice UNSPSC:
12352005
ID PubChem:
329756382
NACRES:
NA.22

product name

N,N′-Disuccinimidyl carbonate, purum, ≥95.0% (NMR)

Grado

purum

Livello qualitativo

200

Saggio

≥95.0% (NMR)

Forma fisica

powder

Impiego in reazioni chimiche

reaction type: Carbonylations

Impurezze

~3% N-hydroxysuccinimide (NMR)

Punto di fusione

190 °C (dec.) (lit.)

applicazioni

peptide synthesis

Temperatura di conservazione

−20°C

Stringa SMILE

O=C1CCC(=O)N1OC(=O)ON2C(=O)CCC2=O

InChI

1S/C9H8N2O7/c12-5-1-2-6(13)10(5)17-9(16)18-11-7(14)3-4-8(11)15/h1-4H2
PFYXSUNOLOJMDX-UHFFFAOYSA-N

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Categorie correlate

Applicazioni

N,N′-Disuccinimidyl carbonate (DSC) can be used to synthesize:
  • Various carbamate derivatives from primary and sterically hindered secondary alcohols by alkoxycarbonylation.
  • Active carbonate resins from 4-hydroxymethylpolystyrene and 4-hydroxymethyl-3-nitrobenzamido resins via hydroxy functional groups.
  • Aza-glycinyl dipeptides, important intermediates for the preparation of various azapeptides.

It may be also used:
  • In the two-step preparation of 5-(6-(azidomethyl)nicotinamido)pentanoic acid, a copper-chelating picolyl azide derivative.
  • To activate the hydroxyl group of the hapten, γ-hydroxyphenylbutazone (HPBZ) so that HPBZ can effectively bind with human serum albumin(HSA)-immunogen to form a hapten-protein conjugate.

Altre note

Convenient reagent for preparing N-succinimidyl esters of N-protected amino acids and other acids; activated carbonate, e.g. synthesis of ureas and carbamates; coupling of ligands to proteins (via lysines).

Pittogrammi

Health hazardExclamation mark
GHS08,GHS07

Avvertenze

Warning

Indicazioni di pericolo

H302,H319,H373

Classi di pericolo

Acute Tox. 4 Oral - Eye Irrit. 2 - STOT RE 2 Oral

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

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificati d'analisi (COA)

Lot/Batch Number
BCCB6748
BCBW0349
BCBT6035
BCBS5912V
BCBS4774V

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T. Kokubo et al.
Journal of the American Chemical Society, 109, 606-606 (1987)
N. Nimura et al.
Analytical Chemistry, 58, 2372-2372 (1986)
Arun K Ghosh et al.
Tetrahedron letters, 33(20), 2781-2784 (1992-05-12)
An efficient and mild method for alkoxycarbonylation of amines is described, utilizing commercially available N,N'-disuccinimidyl carbonate.
M Morpurgo et al.
Journal of biochemical and biophysical methods, 38(1), 17-28 (1999-03-17)
Ligands containing amino or hydroxyl groups were converted to their corresponding activated N-hydroxysuccinimidyl carbamate and carbonate by reaction with disuccinimidyl carbonate (DSC). The latter reagents can be used for the group-specific modification of primary amines as an alternative to the
A.K. Ghosh et al.
Tetrahedron Letters, 33, 2781-2781 (1992)
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Articoli

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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