BOP reagent explained

BOP (benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate) is a reagent commonly used for the synthesis of amides from carboxylic acids and amines in peptide synthesis.[1] [2] It can be prepared from 1-hydroxybenzotriazole and a chlorophosphonium reagent under basic conditions.[3] This reagent has advantages in peptide synthesis since it avoids side reactions like the dehydration of asparagine or glutamine redisues.[4] BOP has used for the synthesis of esters from the carboxylic acids and alcohols.[5] BOP has also been used in the reduction of carboxylic acids to primary alcohols with sodium borohydride (NaBH4).[6] Its use raises safety concerns since the carcinogenic compound HMPA is produced as a stoichiometric by-product.

See also

References

  1. Web site: (Benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 226084. BOP Reagent. 2020-02-11.
  2. Mansour . Tarek S. . Bardhan . Sujata . Wan . Zhao-Kui . 2010 . Phosphonium- and Benzotriazolyloxy-Mediated Bond-Forming Reactions and Their Synthetic Applications . Synlett . en . 2010 . 08 . 1143–1169 . 10.1055/s-0029-1219820 . 0936-5214.
  3. Hoffmann . Frank . Jäger . Lothar . Griehl . Carola . 2003-02-01 . Synthesis and Chemical Constitution of Diphenoxyphosphoryl Derivatives and Phosphonium Salts as Coupling Reagents for Peptide Segment Condensation . Phosphorus, Sulfur, and Silicon and the Related Elements . en . 178 . 2 . 299–309 . 10.1080/10426500307942 . 1042-6507.
  4. Prasad . KVSRG . Bharathi . K . Haseena . Banu B . 2011 . Applications of Peptide Coupling Reagents- An Update . International Journal of Pharmaceutical Sciences Review and Research . 8 . 1 . 108–119.
  5. Kim . Moon H. . Patel . Dinesh V. . 1994-08-01 . “BOP” as a reagent for mild and efficient preparation of esters . Tetrahedron Letters . 35 . 31 . 5603–5606 . 10.1016/S0040-4039(00)77257-1 . 0040-4039.
  6. McGeary . Ross P. . 1998 . Facile and chemoselective reduction of carboxylic acids to alcohols using BOP reagent and sodium borohydride . Tetrahedron Letters . en . 39 . 20 . 3319–3322 . 10.1016/S0040-4039(98)00480-8 . 0040-4039.