Evidence map›Paper›PMID 26279525›Full record

ArticleCarbohydrate research2015

S-Ribosylhomocysteine analogs containing a [4-thio]ribose ring.

Adam J Sobczak, Christiane Chbib, Stanislaw F Wnuk

Open access · greenAbstract read
In one paragraph

Article in Carbohydrate research, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.

0numbers the graph read from it
0cells of the map it votes in
2citing papers in PubMed
0.8field-weighted citation impact, top 27% 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

2 citing papers in PubMed, 5 citations in OpenAlex.

  1. Review
  2. Journal of sulphur chemistry
    Article
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

3 authors at 1 institution in 1 country.

Adam J SobczakDepartment of Chemistry & Biochemistry, Florida International University, Miami, FL 33199, USA.
Christiane ChbibDepartment of Chemistry & Biochemistry, Florida International University, Miami, FL 33199, USA.
Stanislaw F WnukDepartment of Chemistry & Biochemistry, Florida International University, Miami, FL 33199, USA. Electronic address: wnuk@fiu.edu.
Florida International University · US

Funding

Nucleoside and Carbohydrate-based Enzyme InhibitorsSC1CA138176 · NCI · FLORIDA INTERNATIONAL UNIVERSITY · PI WNUK, STANISLAW F · 2008 to 2011
$818k
NCI NIH HHS 1SC1CA138176NCI NIH HHS SC1 CA138176
6 · The paper itself

Abstract

The [4-thio]-S-ribosylhomocysteine (SRH) analogs containing substitution of a sulfur atom for the endocyclic oxygen were synthesized by coupling of the 4-thioribose substrates with a thiolate generated from the protected homocysteine. Coupling of the protected 1-deoxy-5-O-mesyl-S-oxo-4-thio-D-ribofuranose with homocysteinate salt gave the C4 epimers of [4-thio]-SRH at the sulfoxide oxidation level lacking a hydroxyl group at anomeric carbon. Treatment of these sulfoxides with BF3⋅Et2O/NaI affected simultaneous reduction to sulfide and global deprotection affording 1-deoxy-4-thio-SRH analog. Treatment of the protected 1-deoxy-S-oxo-4-thio-D-ribofuranose sulfoxide with DAST/SbCl3 resulted in the fluoro-Pummerer rearrangement to give 4-thio-β-D-ribofuranosyl fluoride. Mesylation of the latter at 5-hydroxyl position followed by coupling with homocysteinate salt and subsequent global deprotection with trifluoroacetic acid afforded [4-thio]-SRH thiohemiacetal.

Indexed as

CarbonHomocysteineHomocystineSulfurTrifluoroacetic AcidCarbonHomocysteineHomocystineS-ribosyl-L-homocysteineSulfurTrifluoroacetic AcidHomocysteineLuxSS-RibosylhomocysteineThioacetalsThiosugars

Identifiers

PMID26279525
PMCPMC4604056
OpenAlexW1150655415

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.