Evidence map›Paper›PMID 35807480›Full record

ArticleMolecules (Basel, Switzerland)2022

Carbodiimide-Mediated Beckmann Rearrangement of Oxyma-B as a Side Reaction in Peptide Synthesis.

Andrea Orlandin, Ivan Guryanov, Lucia Ferrazzano, Barbara Biondi, Francesca Biscaglia, Claudia Storti, Marzio Rancan, Fernando Formaggio, Antonio Ricci, Walter Cabri

Open access · goldAbstract read
In one paragraph

Article in Molecules (Basel, Switzerland), 2022. 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
0.6field-weighted citation impact, top 36% 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, 7 citations in OpenAlex.

  1. Article
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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

10 authors at 3 institutions in 2 countries.

Andrea OrlandinFresenius Kabi iPSUM Srl, Via San Leonardo 23, 45010 Villadose, Italy.
Ivan GuryanovFresenius Kabi iPSUM Srl, Via San Leonardo 23, 45010 Villadose, Italy.
Lucia FerrazzanoDepartment of Chemistry "Giacomo Ciamician", University of Bologna, Via Selmi 2, 40126 Bologna, Italy.
Barbara BiondiICB, Padova Unit, CNR, Department of Chemistry, University of Padova, Via Marzolo 1, 35131 Padova, Italy.ORCID 0000-0003-2393-7333
Francesca BiscagliaICB, Padova Unit, CNR, Department of Chemistry, University of Padova, Via Marzolo 1, 35131 Padova, Italy.
Claudia StortiICB, Padova Unit, CNR, Department of Chemistry, University of Padova, Via Marzolo 1, 35131 Padova, Italy.
Marzio RancanICMATE, CNR, Department of Chemistry, University of Padova, Via Marzolo 1, 35131 Padova, Italy.ORCID 0000-0001-9967-5283
Fernando FormaggioICB, Padova Unit, CNR, Department of Chemistry, University of Padova, Via Marzolo 1, 35131 Padova, Italy.
Antonio RicciFresenius Kabi iPSUM Srl, Via San Leonardo 23, 45010 Villadose, Italy.
Walter CabriFresenius Kabi iPSUM Srl, Via San Leonardo 23, 45010 Villadose, Italy.ORCID 0000-0001-7865-0474
University of Padua · ITUniversity of Bologna · ITSt Petersburg University · RU

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

The suppression of side reactions is one of the most important objectives in peptide synthesis, where highly reactive compounds are involved. Recently, the violuric acid derivative Oxyma-B was introduced into peptide synthesis protocols as a promising additive to efficiently control the optical purity of the amino acids prone to racemization. However, we discovered a side reaction involving the Beckmann rearrangement of Oxyma-B during the coupling reaction, which compromises the yield and purity of the target peptides. Here, we present the investigation of the mechanism of this rearrangement and the optimization of the coupling reaction conditions to control it. These results can be taken into account for the design of novel efficient oxime-based coupling reagents.

Indexed as

CarbodiimidesOximesAmino Acid SequenceBarbituratesPeptides5-(hydroxyimino)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trioneBarbituratesCarbodiimidesOximesPeptidesamino acidBeckman rearrangementcouplingGLP-1glucagonOxyma-Bpeptideracemization

Identifiers

PMID35807480
PMCPMC9268172
OpenAlexW4283743959

What OpenQuestion holds

Textmetadata
LicenceCC BY
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.