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Two-step conversion of unprotected oligosaccharides to generate bioorthogonal oligosaccharide tool compounds.

ABSTRACT: Oligosaccharides have valuable effects in biological systems, but their complex nature makes them difficult to convert into chemical tools. We have developed a two-step conversion of unprotected oligosaccharides that is highly amenable to generating a variety of complex oligosaccharide tool compounds. This sequence features an optimized Kochetkov amination procedure and subsequent amide coupling. With these simple synthetic conversions, the creation of novel bioorthogonal carbohydrate probes becomes easily accessible and new avenues for chemical biology may be opened.•Optimized Kochetkov amination procedure for complex oligosaccharides.•Highly versatile amide coupling for facile probe synthesis.

SUBMITTER: Chambers SA

PROVIDER: S-EPMC7393521 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

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Two-step conversion of unprotected oligosaccharides to generate bioorthogonal oligosaccharide tool compounds.

Chambers Schuyler A SA Townsend Steven D SD

MethodsX 20200716

Oligosaccharides have valuable effects in biological systems, but their complex nature makes them difficult to convert into chemical tools. We have developed a two-step conversion of unprotected oligosaccharides that is highly amenable to generating a variety of complex oligosaccharide tool compounds. This sequence features an optimized Kochetkov amination procedure and subsequent amide coupling. With these simple synthetic conversions, the creation of novel bioorthogonal carbohydrate probes bec ...[more]

PMID: 32760661

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Project description:BACKGROUND:Because of a lack of preference-based health-related quality of life (HRQoL) instruments suitable for infants aged 0-12 months, we previously developed the Infant QoL Instrument (IQI). The present study aimed to generate an algorithm to estimate utilities for the IQI. METHODS:Via an online survey, respondents from the general population and primary caregivers from China-Hong Kong, the UK, and the USA were presented 10 discrete choice scenarios based on the IQI classification system. An additional sample of respondents from the general population were also asked if they considered the examined health states to be worse than death. Coefficients for the IQI item levels were obtained with a conditional logit model based on the responses of the primary caregivers for IQI states only. These coefficients were then normalized using the rank-ordered logit model based on the responses from the general population who assessed "death" as a choice option. In this way, the values were rescaled from full health (1.0) to death (0.0), and consequently, they became suitable for the computation of quality-adjusted life years. RESULTS:The total sample consisted of 1409 members of the general population and 1229 primary caregivers. Results indicated that, out of the 7 IQI items ("sleeping," "feeding," "breathing," "stooling/poo," "mood," "skin," and "interaction"), "breathing" had the highest impact on the HRQoL of infants. Moreover, except for "stooling," all item levels were statistically significant. The general population sample considered none of the health states as worse than death. The utility value for the worst health state was 0.015 (State 4444444). CONCLUSIONS:The IQI is the first generic instrument to assess overall HRQoL in 0-1-year-old infants by providing values and utilities. Using discrete choice experiments, we demonstrated that it is possible to derive utilities of infant health states. The next step will be to collect IQI values in a clinical population of infants and to compare these values with those of other instruments.

Dataset Information

Two-step conversion of unprotected oligosaccharides to generate bioorthogonal oligosaccharide tool compounds.

Publications

Two-step conversion of unprotected oligosaccharides to generate bioorthogonal oligosaccharide tool compounds.

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