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Record W2096147608 · doi:10.1021/mp049959+

Structure and Specificity of a Human Valacyclovir Activating Enzyme:  A Homology Model of BPHL

2004· article· en· W2096147608 on OpenAlexaboutno aff
In‐Sook Kim, Gordon M. Crippen, Gordon L. Amidon

Bibliographic record

VenueMolecular Pharmaceutics · 2004
Typearticle
Languageen
FieldMedicine
TopicHIV/AIDS drug development and treatment
Canadian institutionsnot available
FundersNational Institute of General Medical Sciences
KeywordsActive siteHydrolaseProdrugChemistryStereochemistryDocking (animal)Catalytic triadHomology modelingNucleosideSerineSerine hydrolaseHistidineMolecular modelEnzymeAmino acidBinding siteBiochemistry

Abstract

fetched live from OpenAlex

Biphenyl hydrolase-like (BPHL) protein is a novel serine hydrolase which has been identified as human valacyclovirase (VACVase), catalyzing the hydrolytic activation of valine ester prodrugs of the antiviral drugs acyclovir and ganciclovir as well as other amino acid ester prodrugs of therapeutic nucleoside analogues. The broad specificity for nucleoside analogues as parent drugs suggests that BPHL may be particularly useful as a molecular target for prodrug activation. In order to develop an initial structural view of the specificity of BPHL, a homology model of BPHL based on the crystal structure of 2-hydroxy-6-oxo-7-methylocta-2,4-dienoate hydrolase was developed using the Molecular Operating Environment package (Chemical Computing Group, Montreal, Quebec), evaluated for its stereochemical quality and identification of free cysteines, and used in a molecular docking study. The BPHL model has residues S122, H255, and D227 comprising the putative catalytic triad in proximity and potential charge-charge interaction sites, M52 or D123 for the alpha-amino group. The model also suggested that the structural preference of BPHL for hydrophobic amino acyl promoieties and its limited activity for the secondary alcohol substrates may be attributed to the hydrophobic acyl-binding site formed by residues I158, G161, I162, and L229, and the spatial constraint around the catalytic site by a loop on one side, the active serine and histidine on the other side, and L53 and L179 on top. In addition, the broad specificity for nucleoside analogues may be due to the relatively less constrained nucleoside-binding site opening toward the entrance of the substrate-binding pocket. The homology model of BPHL provides a basis for further investigation of the catalytic and active site residues, can account for the observed structure activity profile of BPHL, and will be useful in the design of nucleoside prodrugs.

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)0.000
metaresearch head score (Gemma)0.000
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 score0.009
Threshold uncertainty score0.598

Codex and Gemma teacher scores by category

CategoryCodexGemma
Metaresearch0.0000.000
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 science0.0000.000
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 head0.033
GPT teacher head0.326
Teacher spread0.293 · 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

Citations18
Published2004
Admission routes1
Has abstractyes

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