title: Enzymatic production of HMO mimics by the sialylation of galacto-oligosaccharides.
abstract: Human milk oligosaccharides (HMOs) are a family of structurally diverse unconjugated glycans that exhibit a wide range of biological activities. In this report, we describe an efficient, Multi-Enzyme One-Pot strategy to produce HMO mimics by the sialylation of galacto-oligosaccharides (GOSs), which are often added to infant formula as an inexpensive alternative to HMOs. In this system, the sialyltransferase donor, cytidine-5'-monophospho-N-acetylneuraminic acid (CMP-Neu5Ac), was generated in situ using a CMP-sialic acid synthetase. The sialylated GOSs were obtained by one-step purification after digesting CMP using the alkaline phosphatase PhoA to cytidine and inorganic phosphate. Although the synthesized α2,3-, α2,6- and α2,3/8-sialyl-GOSs exhibit different sialylation levels and patterns, all of these mixtures can be fermented by Bifidobacterium longum subsp. infantis ATCC 15697 but not by Bifidobacterium adolescentis ATCC 15703. The sialidase NanH2, which is unique to the former strain, hydrolyzed all of the synthesized HMO mimics.
authors: State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin 300071, PR China.
authors: Yuanming
authors: Y
authors: Wang
authors: State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin 300071, PR China.
authors: Kai
authors: K
authors: Jiang
authors: State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin 300071, PR China.
authors: Huanna
authors: H
authors: Ma
authors: State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin 300071, PR China.
authors: Wei
authors: W
authors: Zeng
authors: State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin 300071, PR China; State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, PR China.
authors: Peng G
authors: PG
authors: Wang
authors: Tianjin Key Laboratory of Microbial Functional Genomics, TEDA, Tianjin 300457, PR China.
authors: Nana
authors: N
authors: Yao
authors: State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin 300071, PR China.
authors: Weiqing
authors: W
authors: Han
authors: State Key Laboratory of Medicinal Chemical Biology and College of Pharmacy, Nankai University, Tianjin 300071, PR China. Electronic address: jiansongcheng@nankai.edu.cn.
authors: Jiansong
authors: J
authors: Cheng
authors: Tianjin Key Laboratory of Microbial Functional Genomics, TEDA, Tianjin 300457, PR China.
authors: Wei
authors: W
authors: Wang
mesh_terms: D006279:Health Maintenance Organizations; D006801:Humans; D008895:Milk, Human; D009844:Oligosaccharides / Q000737:chemistry*; D011134:Polysaccharides / Q000737:chemistry*; D056692:Prebiotics
chemical_list: D009844:Oligosaccharides; D011134:Polysaccharides; D056692:Prebiotics
keywords: Galacto-oligosaccharides; Human milk oligosaccharides; Mimics; Prebiotics; Sialyltransferase