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Record W2765122733 · doi:10.1002/9781119092599.ch9

Synthetic Strategies for Macrocyclic Peptides

2017· other· en· W2765122733 on OpenAlexaff
Éric Biron, Simon Vézina‐Dawod, François Bédard

Bibliographic record

Venuenot available
Typeother
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicChemical Synthesis and Analysis
Canadian institutionsUniversité Laval
Fundersnot available
KeywordsChemistryCyclic peptideEpimerPeptideCombinatorial chemistryReagentResidue (chemistry)Disulfide bondStereochemistryPeptide synthesisRing sizeRing (chemistry)Chemical synthesisOrganic chemistryBiochemistry

Abstract

fetched live from OpenAlex

Peptide macrocycles form an outstanding class of natural and synthetic bioactive compounds. This chapter discusses synthetic strategies for the final ring-closing reaction by the widely employed and versatile processes of lactamization, lactonization, and disulfide bridge formation. According to the nature of the chemical bond found in the backbone, cyclic peptides can be classified in two major categories: homodetic peptides and heterodetic peptides. In principle, all methods suitable for peptide bond formation can be applied for head-to-tail macrocyclization of linear peptides; however the reaction usually proceeds more slowly than the corresponding bimolecular version. During synthesis design, the C-terminal amino acid of the linear precursor and the coupling reagent should be carefully chosen to minimize epimerization at the C-terminal residue during cyclization. In many cases, the solution-phase strategy is the best choice for performing the macrocyclization step, especially when larger quantities of cyclic peptide are required.

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 machine prediction

Teacher imitation

Not calibrated prevalence, not ground truth. Human validation pending. The Gemma side is a direct model label for every work in the frame, read from the title-only record. The Codex side is a classifier learned from the 10,348 direct Codex labels and calibrated to design-weighted sample rates; fields without enough sample support carry no Codex call. Candidate is the union of the two sides; consensus is their intersection. These outputs are machine_predicted_unvalidated and are not human labels.

metaresearch head score (Codex)0.000
metaresearch head score (Gemma)0.000
Version: metacan-v3-hybrid-931329e0061cValidation 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: Methods · Consensus signal: Methods
Teacher disagreement score0.007
Threshold uncertainty score0.024

Distilled classifier scores by category (both heads)

CategoryCodexGemma
Metaresearch0.0000.000
Meta-epidemiology (narrow)0.0010.000
Meta-epidemiology (broad)0.0000.000
Bibliometrics0.0010.000
Science and technology studies0.0000.000
Scholarly communication0.0010.001
Open science0.0010.001
Research integrity0.0000.001
Insufficient payload (model declined to judge)0.0070.006

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 head0.011
GPT teacher head0.271
Teacher spread0.260 · 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 source (direct Gemma or distilled Codex), not a consensus.

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

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

Citations9
Published2017
Admission routes1
Has abstractyes

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