In March 2015, Omicron Biochemicals, Inc. was awarded a Small Business Innovation Research (SBIR) grant by the National Institutes of Health (NIH). Our application was submitted and accepted for Funding Opportunity Announcement (FOA) RFA-HD-15-008, "Isolation, Purification, and Synthesis of Human Milk Oligosaccharides with Antimicrobial Activity".

In this Phase I project, a subset of human milk oligosaccharides (HMOs) ranging from disaccharides to pentasaccharides were prepared in multi-gram quantities. All syntheses were conducted under cGLP conditions; existing Omicron documents, procedures, SOPs, methods and laboratory policies developed in prior cGMP projects were modified for use in this work. For each oligosaccharide product, high-resolution ¹H (600 MHz) and ¹³C (150 MHz) NMR data were obtained to confirm structure and purity. This characterization included an effort to assign the ¹H and ¹³C signals as completely as possible, with assistance from 2D homo- and heteronuclear datasets. For each oligosaccharide product, high-resolution mass spectral (HRMS) data was obtained to confirm structural assignments made by NMR, and high-performance liquid chromatography (HPLC) was used to confirm their purity.

The project involved the preparation of kilogram quantities of N-acetyl-lactosamine, and multi-gram quantities of six HMOs: two fucosyl-lactoses 2'FL and 3FL, lacto-N-tetraose (LNT), lacto-N-neotetraose (LNnT), and two lacto-N-fucopentaoses (LNFPs). The aim of this project was to chemically prepare key building block molecules on large scales and basic HMO units on modest scales, and to demonstrate the feasibility of extending the latter basic HMOs to larger sialyl-containing structures via enzymic modification. The utility of integrating chemical and enzymic methods to prepare sialylated HMOs was investigated on a small scale in anticipation of employing this approach to future larger-scale HMO preparations if efficiencies and cost-effectiveness allow.

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