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379115

Sigma-Aldrich

DCC

1.0 M in methylene chloride

Synonym(s):
N,N′-Dicyclohexylcarbodiimide solution
Linear Formula:
C6H11N=C=NC6H11
CAS Number:
Molecular Weight:
206.33
MDL number:
PubChem Substance ID:
NACRES:
NA.22

form

liquid

reaction suitability

reaction type: Coupling Reactions

concentration

1.0 M in methylene chloride

density

1.247 g/mL at 25 °C

application(s)

peptide synthesis

SMILES string

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

InChI key

QOSSAOTZNIDXMA-UHFFFAOYSA-N

Gene Information

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

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Application

DCC (N,N′-Dicyclohexylcarbodiimide) is mainly used to mediate peptide coupling and also to activate carboxylic acids for esterification.

Packaging

100, 800 mL in Sure/Seal™

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Dermal - Carc. 2 - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Central nervous system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

190.4 °F - closed cup

Flash Point(C)

88 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificate of Analysis

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Certificate of Origin

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Liposomes containing alkylated methotrexate analogues for phospholipase A 2 mediated tumor targeted drug delivery.
Kaasgaard T, et al.
Chemistry and Physics of Lipids, 157(2), 94-103 (2009)
Effects of amounts of additives on peptide coupling mediated by a water?soluble carbodiimide in alcohols.
Nozaki S.
The Journal of Peptide Research, 54(2), 162-167 (1999)
Masashi Toei et al.
The Journal of biological chemistry, 288(36), 25717-25726 (2013-07-31)
N,N-Dicyclohexylcarbodiimide (DCCD) is a classical inhibitor of the F0F1-ATP synthase (F0F1), which covalently binds to the highly conserved carboxylic acid of the proteolipid subunit (c subunit) in F0. Although it is well known that DCCD modification of the c subunit
Denys Pogoryelov et al.
Nature chemical biology, 6(12), 891-899 (2010-10-26)
The microscopic mechanism of coupled c-ring rotation and ion translocation in F(1)F(o)-ATP synthases is unknown. Here we present conclusive evidence supporting the notion that the ability of c-rings to rotate within the F(o) complex derives from the interplay between the
Kenji Mizutani et al.
Proceedings of the National Academy of Sciences of the United States of America, 108(33), 13474-13479 (2011-08-05)
The prokaryotic V-ATPase of Enterococcus hirae, closely related to the eukaryotic enzymes, provides a unique opportunity to study the ion-translocation mechanism because it transports Na(+), which can be detected by radioisotope (22Na(+)) experiments and X-ray crystallography. In this study, we

Articles

Carbodiimide-mediated peptide coupling

Carbodiimide-mediated peptide coupling remains to the most frequently used technique.

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