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Record W1865996501 · doi:10.1021/acs.joc.5b02083

Development of an Orthogonal Protection Strategy for the Synthesis of Mycobacterial Arabinomannan Fragments

2015· article· en· W1865996501 on OpenAlexafffund
Kamar Sahloul, Todd L. Lowary

Bibliographic record

VenueThe Journal of Organic Chemistry · 2015
Typearticle
Languageen
FieldChemistry
TopicCarbohydrate Chemistry and Synthesis
Canadian institutionsAlberta Glycomics CentreUniversity of Alberta
FundersCanadian Institutes of Health ResearchAlberta Glycomics CentreBill and Melinda Gates Foundation
KeywordsLipoarabinomannanChemistryGlycosylationTetrasaccharideGlycanMycobacterium tuberculosisAntigenTuberculosisAntibodyCombinatorial chemistryComputational biologyStereochemistryBiochemistryPolysaccharideGlycoproteinImmunologyBiology

Abstract

fetched live from OpenAlex

Mycobacterium tuberculosis, the organism that causes tuberculosis (TB), has a carbohydrate-rich cell wall structure that possesses a number of immunogenic antigens. Circulating antibodies that recognize these glycans are present in patients infected by mycobacteria; detection of these antibodies could be the basis for new TB diagnostics. We describe here the synthesis of a panel of mycobacterial arabinomannan fragments for use in investigations directed at testing the feasibility of such a diagnostic method. In this study, we focused on structural motifs present in the core of the key immunogenic polysaccharide lipoarabinomannan (LAM). To access these compounds, we developed an efficient orthogonal protection strategy that allowed access to seven arabinomannan fragments of LAM (1-7). The targets included one tetrasaccharide, one pentasaccharide, three octasaccharides, and two nonasaccharides. Starting from a differentially protected trimannopyranoside derivative (8 or 9), the targets were obtained using an approach that involved selective removal of the protecting group present at the O-2 position of a single mannopyranoside residue, followed by glycosylation with a pentaarabinofuranose thioglycoside and/or a mannopyranose trichloroacetimidate.

Fetched live from OpenAlex and de-inverted. Abstracts are not stored in this database: the inverted indexes are 8.6 GB of the frame’s 9.3 GB of text, and the host has 13 GB free.

How this classification was reachedexpand

Full frame distilled prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. Learned from the 10,348 direct Codex labels and 10,348 direct Gemma labels. Candidate is the union of thresholded teacher heads; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels or direct frontier model labels.

metaresearch head score (Codex)0.001
metaresearch head score (Gemma)0.000
Version: codex-gemma-dda1882f352aValidation status: machine_predicted_unvalidated
Candidate categoriesnone
Consensus categoriesnone
DomainCandidate signal: none · Consensus signal: none
Study designCandidate signal: Bench or experimental · Consensus signal: Bench or experimental
GenreCandidate signal: Empirical · Consensus signal: Empirical
Teacher disagreement score0.005
Threshold uncertainty score0.857

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.000
Meta-epidemiology (narrow)0.0000.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0000.000
Science and technology studies0.0000.000
Scholarly communication0.0000.000
Open science0.0010.000
Research integrity0.0000.000
Insufficient payload (model declined to judge)0.0010.000

Machine scores (provisional)

The two teacher heads of the student model, read on this work. A score orders the frame for review; it never asserts a category, and the validation status ships verbatim with every row.

Baseline scores from an immature model (maturity gate not passed, 7 training rounds). Scores rank; they never assert a category.

Opus teacher head0.045
GPT teacher head0.249
Teacher spread0.204 · how far apart the two teachers sit on this one work
Validation statusscore_only:v0-immature-baseline · verbatim from the scoring run: score_only means the number may rank works, and no category label ships from it

Classification

machine, unvalidated

Machine predicted; a candidate call from one teacher head, not a consensus.

The models applied no category: nothing in the taxonomy fit this work.
Study designBench or experimental
Domainnot available
GenreEmpirical

How this classification was reached, model by model and score by score, is at the end of the page under "How this classification was reached".

Quick stats

Citations35
Published2015
Admission routes2
Has abstractyes

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