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Chemical Compound Review:

DIPCDI N,N'-dipropan-2- ylmethanediimine

Synonyms: PubChem12717, CCRIS 3413, AG-C-13515, AG-G-69492, AG-G-71170, ...

Cavallaro, V. et al., McMurray, J.S. et al., Shenoy, N.R. et al., Buratti, M. et al., Hayes, B.B. et al., et al.

Falck, Sangras, Capdevila,

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High impact information on NSC 42080

The kinetics of addition of diisopropylcarbodiimide to Cl(3)P=NPr(i)() and subsequent elimination were studied, and rate constants were determined: k(add) = 1.7 x 10(-3) (+/-0.1 x 10(-3)) M s(-1) and k(elim) = 4.0 x 10(-4) (+/-0.3 x 10(-4)) s(-1) [1].
Reagents for carboxyl group activation, including 1,3-dicyclohexylcarbodiimide (DCC), 1,1'-carbonyldiimidazole (CDI), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC), benzotriazol-1-yl-oxy-tris(dimethylamino)phosphonium hexafluorophosphate (BOP), and 1,3-diisopropylcarbodiimide (DICD) were compared [2].
The di-tert-butyl ester was obtained by S-palmitoylation of GSH in TFA as solvent, N-(t)Boc-protection, esterification using (t)BuOH mediated by diisopropylcarbodiimide/copper(I) chloride, and saponification of the thioester [3].
When compared with the more reactive Castro's reagent, the results confirm that DIC in the presence of HOBt can be successfully employed to minimize the formation of intermolecular oligomeric byproducts associated with the preparation of cyclic hGH[6-14] peptide analogues based on an i-->(i + 4)Lys-->Glu or Glu-->Lys cyclization strategy [4].
The use of 1,3-diisopropylcarbodiimide (DIC) for the synthesis of cyclic analogues of the hypoglycaemic peptide fragment derived from the N-terminus of human growth hormone (hGH), namely hGH[6-13], is described [4].

Associations of NSC 42080 with other chemical compounds

Dicyclohexylcarbodiimide (DCC) and diisopropylcarbodiimide (DIC) are two commonly used coupling reagents in protein synthesis resulting in exposure of individuals in chemical and pharmaceutical industries as well as research laboratories involved in protein synthesis and recombinant DNA techniques [5].
A comparison was made between benzotriazoyloxy-tris-(dimethyl-amino)phosphonium hexafluorophosphate (BOP) and diisopropylcarbodiimide (DIPCDI) as cyclization reagents on kieselguhr-supported polydimethylacrylamide, chloromethyl-PolyHipe, and two commercially available polystyrene supports using DMF, CH2Cl2 and THF as cyclization solvents [6].
Methylhippuric acid isomers (MHAs), urinary metabolites of xylenes, were determined, after clean-up by C18-SPE and esterification with hexafluoroisopropanol and diisopropylcarbodiimide, by GC with ECD detection, on an SPB-35 capillary column (30 m, 0.32 mm I.D., 0.25 microm film thickness, beta = 320) [7].

Analytical, diagnostic and therapeutic context of NSC 42080

Diisopropylcarbodiimide was identified as an optimal reagent based on the purity of the product, stability of the reagent, and convenience of handling on plate-based multiple parallel centrifugation synthesizer [8].

References

Catalytic double-bond metathesis without the transition metal. Bell, S.A., Meyer, T.Y., Geib, S.J. J. Am. Chem. Soc. (2002) [Pubmed]
Carboxylic acid-modified polyethylene: a novel support for the covalent immobilization of polypeptides for C-terminal sequencing. Shenoy, N.R., Bailey, J.M., Shively, J.E. Protein Sci. (1992) [Pubmed]
Preparation of N-(t)Boc l-glutathione dimethyl and di-tert-butyl esters: Versatile synthetic building blocks. Falck, J.R., Sangras, B., Capdevila, J.H. Bioorg. Med. Chem. (2007) [Pubmed]
Solid-phase synthesis of cyclic analogues related to the hypoglycaemic peptide hGH(6-13): comparison of two i-->i + 4 lactam cyclization procedures. Cavallaro, V., Thompson, P.E., Hearn, M.T. J. Pept. Sci. (2001) [Pubmed]
Contact hypersensitivity to dicyclohexylcarbodiimide and diisopropylcarbodiimide in female B6C3F1 mice. Hayes, B.B., Gerber, P.C., Griffey, S.S., Meade, B.J. Drug and chemical toxicology. (1998) [Pubmed]
Influence of solid support, solvent and coupling reagent on the head-to-tail cyclization of resin-bound peptides. McMurray, J.S., Lewis, C.A., Obeyesekere, N.U. Pept. Res. (1994) [Pubmed]
Gas chromatography-electron-capture detection of urinary methylhippuric acid isomers as biomarkers of environmental exposure to xylene. Buratti, M., Pellegrino, O., Valla, C., Fustinoni, S., Brambilla, G., Colombi, A. J. Chromatogr. B Biomed. Sci. Appl. (1999) [Pubmed]
Search for optimal coupling reagent in multiple peptide synthesizer. Hachmann, J., Lebl, M. Biopolymers (2006) [Pubmed]

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