Biotechnological production of human milk oligosaccharides

Chemoenzymatic synthesis of lacto-N-tetrasaccharide and sialyl lacto-N-tetrasaccharides

“…9 However, the overall yield is low as the sialylated lactosamine donor was synthesized by two successive galactosidase-and transsialidase-catalyzed reactions. 9 Therefore, a simple and practical approach for the preparation of lacto-N-biose donor and lactoside acceptor building blocks is still highly desirable for convergent synthesis of LNT and its derivatives.…”

“…4 The microbial and coupled enzymatic approaches only have limited success in producing a few LNT related HMOs, and the large scale synthesis is challenging due to the cost and complicated purification processes. 8,9 Recently, a chemoenzymatic approach was developed by Thime and Schmidt for the synthesis of LSTa, which relied on the chemical glycosylation of a lactoside acceptor with an enzymatically produced sialylated lactosamine donor. 9 However, the overall yield is low as the sialylated lactosamine donor was synthesized by two successive galactosidase-and transsialidase-catalyzed reactions.…”

“…8,9 Recently, a chemoenzymatic approach was developed by Thime and Schmidt for the synthesis of LSTa, which relied on the chemical glycosylation of a lactoside acceptor with an enzymatically produced sialylated lactosamine donor. 9 However, the overall yield is low as the sialylated lactosamine donor was synthesized by two successive galactosidase-and transsialidase-catalyzed reactions. 9 Therefore, a simple and practical approach for the preparation of lacto-N-biose donor and lactoside acceptor building blocks is still highly desirable for convergent synthesis of LNT and its derivatives.…”

“…In recent years, several elegant chemical syntheses, [4][5][6][7] microbial and coupled enzymatic approaches, 8,9 and chemoenzymatic synthesis 10 have been developed for the synthesis of LNT and its derivatives. The reactivity-based one-pot synthesis has been demonstrated as a valuable way to prepare LNT and fucosyl LNT in a few steps from several specifically designed building blocks, 5 however, this strategy may not be amenable to preparation of other structurally similar HMOs.…”

Synthesis of lacto- N -tetraose

“…In contrast, LNnT is more common in bovine milk and by extension more common in infant formula. 28 The relative intensities of this peak will vary from sample to sample as LNT and/or LNnT undergoes enzymatic functionalization to larger, fucosylated derivatives. Unlike LNnT, LNT is not currently available at large scale through chemo-enzymatic synthesis.…”