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Details

Stereochemistry ABSOLUTE
Molecular Formula C12H21N3O3
Molecular Weight 255.3134
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PYRROLYSINE

SMILES

C[C@@H]1CC=N[C@H]1C(=O)NCCCC[C@H](N)C(O)=O

InChI

InChIKey=ZFOMKMMPBOQKMC-KXUCPTDWSA-N
InChI=1S/C12H21N3O3/c1-8-5-7-14-10(8)11(16)15-6-3-2-4-9(13)12(17)18/h7-10H,2-6,13H2,1H3,(H,15,16)(H,17,18)/t8-,9+,10-/m1/s1

HIDE SMILES / InChI

Molecular Formula C12H21N3O3
Molecular Weight 255.3134
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
The genome sequence of Methanohalophilus mahii SLP(T) reveals differences in the energy metabolism among members of the Methanosarcinaceae inhabiting freshwater and saline environments.
2010-12-23
Archaeal protein biogenesis: posttranslational modification and degradation.
2010-09-30
Fidelity in archaeal information processing.
2010-09-05
Precision control of cellular pathways with light.
2010-09-03
Selenocysteine, pyrrolysine, and the unique energy metabolism of methanogenic archaea.
2010-08-17
N6-(2-(R)-propargylglycyl)lysine as a clickable pyrrolysine mimic.
2010-08-02
[Expanding genetic code: amino acids 21 and 22--selenocysteine and pyrrolysine].
2010-08
Dual functions of codons in the genetic code.
2010-08
The T box regulatory element controlling expression of the class I lysyl-tRNA synthetase of Bacillus cereus strain 14579 is functional and can be partially induced by reduced charging of asparaginyl-tRNAAsn.
2010-07-22
[Pyrrolysyl-tRNA synthetase-tRNA(Pyl) structure reveals the molecular basis of orthogonality].
2010-07
In silico identification of the sea squirt selenoproteome.
2010-05-10
Modal codon usage: assessing the typical codon usage of a genome.
2010-04
Distinct genetic code expansion strategies for selenocysteine and pyrrolysine are reflected in different aminoacyl-tRNA formation systems.
2010-01-21
Structural clones of UAG decoding RNA.
2009-12
Translation termination in pyrrolysine-utilizing archaea.
2009-11-03
A method for genetically installing site-specific acetylation in recombinant histones defines the effects of H3 K56 acetylation.
2009-10-09
[Pyrrolysyl-tRNA synthetase-tRNA(Pyl) structure reveals the molecular basis of orthogonality].
2009-09
Metal-binding affinity and selectivity of nonstandard natural amino acid residues from DFT/CDM calculations.
2009-08-27
Hacking the genetic code of mammalian cells.
2009-07-06
Pyrrolysyl-tRNA synthetase-tRNA(Pyl) structure reveals the molecular basis of orthogonality.
2009-02-26
Recognition of non-alpha-amino substrates by pyrrolysyl-tRNA synthetase.
2009-02-06
Specificity of pyrrolysyl-tRNA synthetase for pyrrolysine and pyrrolysine analogs.
2009-01-30
One ancestor for two codes viewed from the perspective of two complementary modes of tRNA aminoacylation.
2009-01-27
RamA, a protein required for reductive activation of corrinoid-dependent methylamine methyltransferase reactions in methanogenic archaea.
2009-01-23
A pyrrolysine analogue for site-specific protein ubiquitination.
2009
A facile system for encoding unnatural amino acids in mammalian cells.
2009
A pyrrolysine analogue for protein click chemistry.
2009
Multistep engineering of pyrrolysyl-tRNA synthetase to genetically encode N(epsilon)-(o-azidobenzyloxycarbonyl) lysine for site-specific protein modification.
2008-11-24
Misacylation of pyrrolysine tRNA in vitro and in vivo.
2008-10-15
Structure of Desulfitobacterium hafniense PylSc, a pyrrolysyl-tRNA synthetase.
2008-09-26
Evolutionary patterns in the sequence and structure of transfer RNA: a window into early translation and the genetic code.
2008-07-30
Adding l-lysine derivatives to the genetic code of mammalian cells with engineered pyrrolysyl-tRNA synthetases.
2008-07-11
Trends in selenium utilization in marine microbial world revealed through the analysis of the global ocean sampling (GOS) project.
2008-06-13
Crystallographic studies on multiple conformational states of active-site loops in pyrrolysyl-tRNA synthetase.
2008-05-02
[Non-standard genetic codes and translation termination].
2008-03-06
Comparative genomic analyses of copper transporters and cuproproteomes reveal evolutionary dynamics of copper utilization and its link to oxygen.
2008-01-02
Adding pyrrolysine to the Escherichia coli genetic code.
2007-11-13
Critical roles for a genetic code alteration in the evolution of the genus Candida.
2007-10-31
Evolution of the genetic code: partial optimization of a random code for robustness to translation error in a rugged fitness landscape.
2007-10-23
Translation: duality in the genetic code.
2007-08-30
The amino-terminal domain of pyrrolysyl-tRNA synthetase is dispensable in vitro but required for in vivo activity.
2007-07-10
Mining prokaryotic genomes for unknown amino acids: a stop-codon-based approach.
2007-06-28
Class I and class II lysyl-tRNA synthetase mutants and the genetic encoding of pyrrolysine in Methanosarcina spp.
2007-06
Novel tRNA aminoacylation mechanisms.
2007-06
Flexible mapping of homology onto structure with homolmapper.
2007-04-11
Query-dependent banding (QDB) for faster RNA similarity searches.
2007-03-30
Hon-yaku: a biology-driven Bayesian methodology for identifying translation initiation sites in prokaryotes.
2007-02-08
Natural expansion of the genetic code.
2007-01
A genetic code alteration generates a proteome of high diversity in the human pathogen Candida albicans.
2007
The genetic code--40 years on.
2007
Substance Class Chemical
Created
by admin
on Mon Mar 31 23:33:26 GMT 2025
Edited
by admin
on Mon Mar 31 23:33:26 GMT 2025
Record UNII
H3214Y96LP
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRROLYSINE [MI]
Preferred Name English
PYRROLYSINE
MI  
Systematic Name English
L-PYRROLYSINE
Systematic Name English
N6-(((2R,3R)-3-METHYL-3,4-DIHYDRO-2H-PYRROL-2-YL)CARBONYL)-L-LYSINE
Systematic Name English
Code System Code Type Description
PUBCHEM
5460671
Created by admin on Mon Mar 31 23:33:26 GMT 2025 , Edited by admin on Mon Mar 31 23:33:26 GMT 2025
PRIMARY
EPA CompTox
DTXSID70420110
Created by admin on Mon Mar 31 23:33:26 GMT 2025 , Edited by admin on Mon Mar 31 23:33:26 GMT 2025
PRIMARY
CAS
448235-52-7
Created by admin on Mon Mar 31 23:33:26 GMT 2025 , Edited by admin on Mon Mar 31 23:33:26 GMT 2025
PRIMARY
WIKIPEDIA
Pyrrolysine
Created by admin on Mon Mar 31 23:33:26 GMT 2025 , Edited by admin on Mon Mar 31 23:33:26 GMT 2025
PRIMARY
CHEBI
21860
Created by admin on Mon Mar 31 23:33:26 GMT 2025 , Edited by admin on Mon Mar 31 23:33:26 GMT 2025
PRIMARY
CHEBI
58499
Created by admin on Mon Mar 31 23:33:26 GMT 2025 , Edited by admin on Mon Mar 31 23:33:26 GMT 2025
PRIMARY
FDA UNII
H3214Y96LP
Created by admin on Mon Mar 31 23:33:26 GMT 2025 , Edited by admin on Mon Mar 31 23:33:26 GMT 2025
PRIMARY
MERCK INDEX
m9403
Created by admin on Mon Mar 31 23:33:26 GMT 2025 , Edited by admin on Mon Mar 31 23:33:26 GMT 2025
PRIMARY Merck Index