Tropical Journal of Pharmaceutical Research

Original Research Article | OPEN ACCESS

Chemo-enzymatic synthesis of Neu5Gc-containing sialylated lactulose

Jie Zeng , Tian Jia, Yajie Hu, Ruiyao Zhang, Junliang Sun, Bangbang Li, Haiyan Gao

School of Food Science, Henan Institute of Science and Technology, Xinxiang, 453003, China;

For correspondence:- Jie Zeng Email: zengjie623@163.com Tel:+8615836058250

Received: 18 February 2017 Accepted: 17 June 2017 Published: 01 August 2017

Citation: Zeng J, Jia T, Hu Y, Zhang R, Sun J, Li B, et al. Chemo-enzymatic synthesis of Neu5Gc-containing sialylated lactulose. Trop J Pharm Res 2017; 16(7):1655-1662 doi: 10.4314/tjpr.v16i7.26

© 2017 The authors.
This is an Open Access article that uses a funding model which does not charge readers or their institutions for access and distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0) and the Budapest Open Access Initiative (http://www.budapestopenaccessinitiative.org/read), which permit unrestricted use, distribution, and reproduction in any medium, provided the original work is properly credited..

Abstract

Purpose: To synthesize novel sialylated lactuloses, namely, Neu5Gc-α2,3-lactulose and Neu5Gc-α2,6-lactulose.

Methods: ManNGc was chemically synthesized from commercially available N-acetylmannosaime (ManNAc), which was used as the donor substrate to synthesize α-(2→3) linkage and α-(2→6) linkage sialyllactulose from lactulose via sialyltransferases-catalyzed one-pot multienzyme (OPME) approach. The sialylated products were purified by silica gel flash chromatography column. Mass spectrometry (MS) and nuclear magnetic resonance (NMR) were used to confirm the purity and characterize the structure of the new compounds.

Results: Sialyllactulose with α-(2→3) linkage (Neu5Gc-α2,3-lactulose) and α-(2→6) linkage (Neu5Gc-α2,6-lactulose) were efficiently synthesized by an efficient one-pot multienzyme sialylation approach from ManNGc, sodium pyruvate, CTP, and lactulose. The molecular weight of the two products, based on mass spectral data was 648 Da while NMR data indicated the formation of sialylated glycans.

Conclusion: Novel sialylated oligosaccharides have been efficiently synthesized from lactulose using highly efficient OPME sialylation approaches. Further investigations are required to ascertain the probiotic activities for possible applications in pharmaceutical and food industries.

Keywords: Neu5Gc, Chemo-enzymatic synthesis, Sialylation, Sialyllactulose, Lactulose