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43720

Sigma-Aldrich

N,N′-Disuccinimidyl carbonate

≥95.0% (NMR), for peptide synthesis

Sinônimo(s):

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

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About This Item

Fórmula empírica (Notação de Hill):
C9H8N2O7
Número CAS:
Peso molecular:
256.17
Beilstein:
1499137
Número CE:
Número MDL:
Código UNSPSC:
12352005
ID de substância PubChem:
NACRES:
NA.22

product name

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

grau

purum

Nível de qualidade

Ensaio

≥95.0% (NMR)

forma

powder

adequação da reação

reaction type: Carbonylations

Impurezas

~3% N-hydroxysuccinimide (NMR)

pf

190 °C (dec.) (lit.)

aplicação(ões)

peptide synthesis

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

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

chave InChI

PFYXSUNOLOJMDX-UHFFFAOYSA-N

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Aplicação

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.

Outras notas

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).

Pictogramas

Health hazardExclamation mark

Palavra indicadora

Warning

Frases de perigo

Classificações de perigo

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

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

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


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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.
A.K. Ghosh et al.
Tetrahedron Letters, 33, 2781-2781 (1992)
Active carbonate resins for solid-phase synthesis through the anchoring of a hydroxyl function. Synthesis of cyclic and alcohol peptides
Alsina J, et al.
Tetrahedron Letters, 38(5), 883-886 (1997)
Yesica Garcia-Ramos et al.
Journal of peptide science : an official publication of the European Peptide Society, 19(12), 725-729 (2013-11-10)
Aza-glycinyl dipeptides are useful building blocks for the synthesis of a diverse array of azapeptides. The construction of the aza-glycine residue is however challenging, because of the potential for side reactions, such as those leading to formation of oxadiazalone, hydantoin

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