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36650

Sigma-Aldrich

DCC

≥99.0% (GC), for peptide synthesis

Sinônimo(s):

N,N′-Dicyclohexylcarbodiimide

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About This Item

Fórmula linear:
C6H11N=C=NC6H11
Número CAS:
538-75-0
Peso molecular:
206.33
Beilstein:
610662
Número CE:
208-704-1
Número MDL:
MFCD00011659
Código UNSPSC:
12352000
ID de substância PubChem:
329755430
NACRES:
NA.22

product name

DCC, puriss., ≥99.0% (GC)

grau

puriss.

Nível de qualidade

200

Ensaio

≥99.0% (GC)

forma

solid

adequação da reação

reaction type: Coupling Reactions

pb

122-124 °C/6 mmHg (lit.)

pf

32.0-37.0 °C
34-35 °C (lit.)

solubilidade

methylene chloride: 0.1 g/mL, clear, colorless

aplicação(ões)

peptide synthesis

cadeia de caracteres SMILES

C1CCC(CC1)N=C=NC2CCCCC2

InChI

1S/C13H22N2/c1-3-7-12(8-4-1)14-11-15-13-9-5-2-6-10-13/h12-13H,1-10H2

chave InChI

QOSSAOTZNIDXMA-UHFFFAOYSA-N

Informações sobre genes

human ... EPHX2(2053)
mouse ... Ephx2(13850)

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Descrição geral

DCC is an organic compound widely used as a coupling reagent in peptide synthesis. It is also employed as an efficient dehydrating agent for the preparation of amides, esters, nitriles, and anhydrides. Alcohols can be converted into aldehydes and ketone by Moffatt oxidation reaction in the presence of DCC and dimethyl sulfoxide (DMSO).

Aplicação

DCC may be used to promote the esterification of 7-((tert-butyldimethylsilyl)oxy)hepta-2,4-diyn-1-ol with propiolic acid to form 7-((tert-butyldimethylsilyl)oxy)hepta-2,4-diyn-1-yl propynoate.
It may be also used to synthesize:
  • 1,3-Thiazetedine derivatives via [2+2] cycloaddition with 2-phenylethenyl- and 2-(4-nitrophenyl)ethenyl isothiocyanates.
  • 1,3,5-Oxadiazine-4-thiones via [4+2] cycloaddition with benzoyl isothiocyanates.
  • Sterically hindered 1,3,4-oxadiazole derivatives by reacting with (N-isocyanimino)triphenylphosphorane the presence of aromatic (or heteroaromatic) carboxylic acids.

Outras notas

Coupling reagent, reagent for dehydrations etc. Modifies bovine heart mitochondrial transhydrogenase; Inhibition of F1F0-ATPase and other proton-translocating enzymes

Pictogramas

Skull and crossbonesCorrosion
GHS06,GHS05

Palavra indicadora

Danger

Frases de perigo

H302,H311,H317,H318

Classificações de perigo

Acute Tox. 3 Dermal - Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1

Código de classe de armazenamento

6.1D - Non-combustible acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects

Classe de risco de água (WGK)

WGK 3

Ponto de fulgor (°F)

235.4 °F - closed cup

Ponto de fulgor (°C)

113 °C - closed cup

Equipamento de proteção individual

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

Escolha uma das versões mais recentes:

Certificados de análise (COA)

Lot/Batch Number
WXBD6453V
WXBD6647V
WXBD3874V
WXBD2750V
WXBD1829V

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Review of synthesis of 1, 3, 4-oxadiazole derivatives.
Patel K D, et al.
Synthetic Communications, 44(13), 1859-1875 (2014)
Light-dependent chemical modification of thylakoid membrane protein with carboxyl-directed reagents.
J A Laszlo et al.
Archives of biochemistry and biophysics, 215(2), 571-581 (1982-05-01)
R M Pennington et al.
The Journal of biological chemistry, 256(17), 8963-8969 (1981-09-10)
Dicyclohexylcarbodiimide (DCCD) inhibits the reduction of oxidized 3-acetylpyridine adenine dinucleotide (AcPyAD+) by NADPH catalyzed by purified and bovine heart submitochondrial particle transhydrogenase. Kinetic studies demonstrate that the modification of 1 residue results in complete inactivation. Both transhydrogenase preparations were labeled
M. Solioz
Trends in Biochemical Sciences, 9, 309-309 (1984)
Dicyclohexylcarbodiimide (DCC)
Kvasnica M
Synlett, 2007(14), 2306-2307 (2007)
Exibir todos os documentos relacionados

Artigos

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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