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Record W2162689120 · doi:10.1002/ejic.201100142

SiFA‐Modified Phenylalanine: A Key Compound for the Efficient Synthesis of <sup>18</sup>F‐Labelled Peptides

2011· article· en· W2162689120 on OpenAlexaff
L. Iovkova, Daniel Könning, Björn Wängler, Ralf Schirrmacher, Sebastian Schoof, Hans‐Dieter Arndt, Klaus Jurkschat

Bibliographic record

VenueEuropean Journal of Inorganic Chemistry · 2011
Typearticle
Languageen
FieldBiochemistry, Genetics and Molecular Biology
TopicChemical Synthesis and Analysis
Canadian institutionsMcGill UniversityMontreal Neurological Institute and Hospital
FundersDeutsche Forschungsgemeinschaft
KeywordsChemistryPeptide synthesisPhenylalanineStereoselectivityStereochemistryAmino acidFluorinePeptideOrganic chemistryCatalysis

Abstract

fetched live from OpenAlex

Abstract Both the racemic and the stereoselective synthesis of the silicon‐modified amino acid p ‐( t Bu 2 FSi)C 6 H 4 CH 2 (NH 2 )COOH (SiFA‐phenylalanine, 6 ) and its derivatives p ‐( t Bu 2 FSi)C 6 H 4 CH 2 (NHBoc)COOH ( 10 ) and p ‐( t Bu 2 FSi)C 6 H 4 CH 2 (NHFmoc)COOH ( 11 ) are reported. The latter two compounds are valuable building blocks for the convenient introduction of silicon‐based fluoride acceptors (SiFAs) into peptides by solid‐phase peptide syntheses (SPPS). As prove of principle, the Tyr 3 ‐octreotate derivatives 12 , 13 and 14 were prepared by using standard protocols of the solid‐phase peptide synthesis (SPPS). They were labelled with 18 F‐fluorine by isotopic exchange in radiochemical yields of up to 70 % (with radiochemical purity ranging between 92 and 99 %). The incorporation of 18 F‐fluorine into the SiFA‐modified amino acid 6 was studied as the latter may also serve as a tracer in PET. After purification, [ 18 F]‐ 6 showed a remarkable stability in an isotonic solution. Also reported is the molecular structure, as determined by single‐crystal X‐ray diffraction analysis, of p ‐( t Bu 2 FSi)C 6 H 4 CHCH[C(O)OMe]NHC(O)OCH 2 Ph ( 8 ), which serves as a precursor for the stereoselective synthesis of compound 6 .

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)0.001
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 score0.008
Threshold uncertainty score0.642

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0010.001
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)0.0000.000

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 head0.018
GPT teacher head0.212
Teacher spread0.194 · 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

Citations22
Published2011
Admission routes1
Has abstractyes

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