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43720

Sigma-Aldrich

Di-(N-succinimidyl)-carbonat

≥95.0% (NMR), for peptide synthesis

Synonym(e):

N-Succinimidyl-carbonat, DSC

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About This Item

Empirische Formel (Hill-System):
C9H8N2O7
CAS-Nummer:
74124-79-1
Molekulargewicht:
256.17
Beilstein:
1499137
EG-Nummer:
277-730-3
MDL-Nummer:
MFCD00009767
UNSPSC-Code:
12352005
PubChem Substanz-ID:
329756382
NACRES:
NA.22

Produktbezeichnung

Di-(N-succinimidyl)-carbonat, purum, ≥95.0% (NMR)

Qualität

purum

Qualitätsniveau

200

Assay

≥95.0% (NMR)

Form

powder

Eignung der Reaktion

reaction type: Carbonylations

Verunreinigungen

~3% N-hydroxysuccinimide (NMR)

mp (Schmelzpunkt)

190 °C (dec.) (lit.)

Anwendung(en)

peptide synthesis

Funktionelle Gruppe

imide

Lagertemp.

−20°C

SMILES String

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

InChIKey

PFYXSUNOLOJMDX-UHFFFAOYSA-N

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Verwandte Kategorien

Anwendung

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.

Sonstige Hinweise

Reagens zur bequemen Herstellung von N-Succinimidylestern aus N-geschützten Aminosäuren und anderen Säuren; aktiviertes Carbonat, z.B. Synthese von Ureaten and Carbamaten; Koppelung von Liganden an Proteine (über Lysinreste).

Piktogramme

Health hazardExclamation mark
GHS08,GHS07

Signalwort

Warning

Gefahreneinstufungen

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

Lagerklassenschlüssel

11 - Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

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

Hier finden Sie alle aktuellen Versionen:

Analysenzertifikate (COA)

Lot/Batch Number
BCCB6748
BCBW0349
BCBT6035
BCBS5912V
BCBS4774V

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Die Dokumentenbibliothek aufrufen

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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Artikel

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).

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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