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1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride is used as a carboxyl activating agent. It is used in peptide synthesis, 3'-amino-3'-deoxyadenosine-5'-di- and triphosphates and in the preparation of antibodies like immunoconjugates. It plays a vital role for immobilization of large biomolecules in association with N-hydroxysuccinimide. It is also used in the acylation of phosphoranes.
'Water-soluble carbodiimide', widely used for peptide coupling (see Appendix 6), with the major advantage that excess reagent and the urea by-product can be easily removed by washing with dilute acid or water: J. Org. Chem., 26, 2525 (1961); J. Am. Chem. Soc., 87, 2492 (1965). For discussion of the mechanism of peptide coupling with this reagent, see: J. Am. Chem. Soc., 103, 7090 (1981).
Often used in conjunction with an additive such as HOBt (1-hydroxybenzotriazole hydrate) to suppress racemization; see, for example: Bull. Chem. Soc. Jpn., 55, 2165 (1982). A two-phase solvent system (dichloromethane-water or isopropyl acetate-water) has been found to give superior results in this type of peptide coupling: J. Org. Chem., 60, 3569 (1995). In a comparative study, submolar quantities HOBt in DMF-water gave good results: Chem. Lett., 1 (1997).
For use in the synthesis of cyclic derivatives of 3'-amino-3'-deoxyadenosine-5'-di- and triphosphates, see: Angew. Chem. Int. Ed., 33, 1394 (1994).
Promotes various other N-acylation reactions such as the formation of N-acylsulfonamides from primary sulfonamides and N-protected amino acids in the presence of DMAP: Synlett, 1141 (1995).
For use in the acylation of phosphoranes, see (Cyanomethyl)triphenylphosphonium chloride, A13096.
Liu, J. A.; Guo, X. P.; Liang, S.; An, F.; Shen, H. Y.; Xu, Y. J. Regioselective synthesis of 5'-amino acid esters of some nucleosides via orthogonal protecting protocol. Tetrahedron 2015, 71 (9), 1409-1412.
Meng, H.; Zheng, J.; Wen, X.; Cai, Z.; Zhang, J.; Chen, T. pH- and Sugar-Induced Shape Memory Hydrogel Based on Reversible Phenylboronic Acid-Diol Ester Bonds. Macromol. Rapid Commun. 2015, 36 (6), 533-537.
Hazard Statements: H315-H319-H335
Causes skin irritation. Causes serious eye irritation. May cause respiratory irritation.
Precautionary Statements: P261-P280a-P305+P351+P338-P304+P340-P405-P501a
Avoid breathing dust/fume/gas/mist/vapours/spray. Wear protective gloves and eye/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF INHALED: Remove to fresh air and keep at rest in a position comfortable for breathing. Store locked up. Dispose of contents/container in accordance with local/regional/national/international regulations.