Evidence map›Paper›PMID 23227909›Full record

ArticleThe Journal of organic chemistry2013

D-Glucosamine-derived synthons for assembly of L-threo-sphingoid bases. Total synthesis of rhizochalinin C.

Jaeyoung Ko, Tadeusz F Molinski

Abstract read
PubMed Full text at PMC Publisher
In one paragraph

Article in The Journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.

0numbers the graph read from it
0cells of the map it votes in
1citing papers in PubMed
1.0field-weighted citation impact, top 23% of its field
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

1 citing paper in PubMed, 12 citations in OpenAlex.

  1. Review
4 · The record

Corrections and comments

PubMed lists nothing against this paper. Absence here is not a guarantee, only a check that was made.

5 · Who and what money

Authors and funding

2 authors at 1 institution in 1 country.

Jaeyoung KoDepartment of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, La Jolla, California 92093-0358, USA.
Tadeusz F Molinski
Amorepacific (South Korea) · KR

Funding

Antifungals from Marine Invertebrates--AIDS AdjuvantsR01AI039987 · NIAID · UNIVERSITY OF CALIFORNIA, SAN DIEGO · PI MOLINSKI, TADEUSZ F · 1997 to 2010
$2.9M
Natural Products for Treatment of Emergent AIDS-Related PathogensR01AI100776 · NIAID · UNIVERSITY OF CALIFORNIA, SAN DIEGO · PI MOLINSKI, TADEUSZ F · 2012 to 2016
$1.9M
Acquisition of a High Resolution TOF Mass SpectrometerS10RR025636 · NCRR · UNIVERSITY OF CALIFORNIA, SAN DIEGO · PI MOLINSKI, TADEUSZ F · 2010 to 2010
$305k
NCRR NIH HHS S10 RR025636NIAID NIH HHS AI039978NIAID NIH HHS AI100776NIAID NIH HHS R01 AI039987NIAID NIH HHS R01 AI100776
6 · The paper itself

Abstract

A five-step transformation of D-glucosamine, commencing with indium-mediated Barbier reaction without isolation of intermediates, into (R,R)-2-aminohex-5-ene-1,3-diol in 45-51% is described. The latter is a useful synthon for assembly of L-threo-sphingoid bases: long-chain aminoalkanols and aminoalkanediols with configurations antipodal to that found in mammalian D-erythro-sphingosine but prevalent among invertebrate-derived sphingolipids. The utility of the method is demonstrated by the first total synthesis of rhizochalinin C, the long-chain, "two-headed" sphingoid base aglycon of the natural product rhizochalin C from the marine sponge Rhizochalina incrustata.

Indexed as

Biological ProductsGlucosamineGlycosphingolipidsMagnetic Resonance SpectroscopyMolecular StructureRhizoctoniaSphingosineBiological Productserythro-(2R,3S)-sphingosineGlucosamineGlycosphingolipidsrhizochalin CSphingosine

Identifiers

PMID23227909
PMCPMC3548972
OpenAlexW2075117619

What OpenQuestion holds

Textmetadata
LicenceTDM
Read underepoch 390

Registered trials

None linked

Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.