43720

Di-(N-succinimidyl)-carbonat

≥95.0% (NMR), for peptide synthesis

• Synonym(e): N-Succinimidyl-carbonat, DSC
• Empirische Formel (Hill-System): C₉H₈N₂O₇
• CAS-Nummer: 74124-79-1
• Molekulargewicht: 256.17
• NACRES: NA.22
• PubChem Substance ID: 329756382
• UNSPSC Code: 12352005
• EC Number: 277-730-3
• MDL number: MFCD00009767
• Beilstein/REAXYS Number: 1499137

Eigenschaften

• Produktname: Di-(N-succinimidyl)-carbonat, purum, ≥95.0% (NMR)
• grade: purum
• Quality Segment: 200
• assay: ≥95.0% (NMR)
• form: powder
• reaction suitability: reaction type: Carbonylations
• impurities: ~3% N-hydroxysuccinimide (NMR)
• mp: 190 °C (dec.) (lit.)
• application(s): peptide synthesis
• functional group: imide
• storage temp.: −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
• InChI key: PFYXSUNOLOJMDX-UHFFFAOYSA-N

Beschreibung

Application

N,N′-Disuccinimidyl carbonate (DSC) can be used to synthesize:

• Various carbamate derivatives from primary and sterically hindered secondary alcohols by alkoxycarbonylation.[1]
• 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.[2]

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.

Other Notes

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).[3]

Sicherheitshinweise

• signalword: Warning
• Lagerklasse: 11 - Combustible Solids
• wgk: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• pictograms: GHS07
• hcodes: H302
• pcodes: P264 - P270 - P301 + P312 - P501
• Hazard Classifications: Acute Tox. 4 Oral