Chem. J. Chinese Universities ›› 2010, Vol. 31 ›› Issue (4): 718.

• Articles • Previous Articles     Next Articles

Reduction of the Aromatic Nitro Group in Peptide by Ammonium Formate Catalytic Transfer Hydrogenation——An Indirect Introduction of p-Aminophenylalanine into Peptide Chain

GAO Yong-Qing1,2, ZHOU Ning2, LÜ Yu-Jian2, SHI Wei-Guo2, CHENG Mao-Sheng1, LIU Ke-Liang2*   

  1. 1. School of Pharmaceutical Engineering, Shenyang Pharmaceutical University, Shenyang 110016, China;
    2. Beijing Institute of Pharmacology and Toxicology, Academy of Military Medical Sciences, Beijing 100850, China
  • Received:2009-05-18 Online:2010-04-10 Published:2010-04-10
  • Contact: LIU Ke-Liang. E-mail: keliangliu@yahoo.com
  • Supported by:

    国家自然科学基金(批准号: 30500629)和国家重大新药创制科技重大专项基金(批准号: 2009ZX09301-002, 2009ZX09103-027)资助.

Abstract:

The p-aminophenylalanine was a useful functional amino acid in the design of peptide drugs, and it was usually prepared by the reduction of p-nitrophenylalanine. Ammonium formate catalytic transfer hydrogenation(AF-CTH) was confirmed feasible in transforming the aromatic nitro group into the amino group in a dipeptide, and the orthogonal protection for p-aminophenylalanine in traditional route could be avoided in this method. Therefore, we wondered if this method could be widely used for the reduction of p-nitrophenylalanine residue in various peptides, such as the MSH(tetrapeptide), LHRH(decapeptide) and dynorphin(heptadecapeptide) analogues. The reduction processes were monitored by HPLC and the results showed that all sequences could be smoothly transformed into the desired products, except the LHRH analogue containing p-chlorophenylalanine due to the dechlorination. It suggested that AF-CTH was an effective method for the reduction of the nitro group in a peptide. In addition, it was found that the reduction rate of the nitro group was slower in longer peptide and not obviously correlative to its site in peptide.

Key words: Melanocyte-stimulating hormones(MSH); Luteinizing hormone-releasing hormone(LHRH); Dynorphin; Ammonium formate catalytic transfer hydrogenation; Nitro group reduction

TrendMD: