Synthesis of lacto-N-tetraose

Human milk oligosaccharides (HMOs) are the third largest macromolecular component of breast milk and offer infants numerous health benefits, most of which stem from the development of a healthy microbiome. Characterization, quantification, and chemical derivatization of HMOs remains a frontier issue...

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Bibliographic Details
Published in:Carbohydrate research 2017-02, Vol.440-441, p.43-50
Main Authors: Craft, Kelly M., Townsend, Steven D.
Format: Article
Language:English
Subjects:
Acetamides - chemistry
Carbohydrate Conformation
Carbohydrate Sequence
Female
Glycomics
Humans
Milk, Human - chemistry
Oligosaccharides - chemical synthesis
Oligosaccharides - isolation & purification
Pyrans - chemistry
Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
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Summary:Human milk oligosaccharides (HMOs) are the third largest macromolecular component of breast milk and offer infants numerous health benefits, most of which stem from the development of a healthy microbiome. Characterization, quantification, and chemical derivatization of HMOs remains a frontier issue in glycobiology due to the challenge of isolating appreciable quantities of homogenous HMOs from breast milk. Herein, we report the synthesis of the human milk tetrasaccharide lacto-N-tetraose (LNT). LNT is ubiquitous in human breast milk as it is a core structure common to longer-chain HMOs and many glycolipids. [Display omitted] •MALDI FT ICR analysis of human milk.•Gram Scale synthesis of protected Lacto-N-Tetraose (LNT).•Interesting trapping of acyloxonium ion, resulting from participation of a C2 acetate during a glycosylation event.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2017.02.001