Lysidine - CAS 116120-47-9

Catalog number: BRB-003

Lysidine is a vital molecule used in the synthesis of transfer RNA (tRNA), serving as a modified base. This product excels in the management of various diseases related to tRNA metabolism disorders, such as lysine-related leukoencephalopathy. Its high purity and efficacy make it an essential tool for researchers and scientists in the biomedical field.

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Synonyms

L-Lysine, N6-(4-amino-1-β-D-ribofuranosyl-2(1H)-pyrimidinylidene)-, hydrochloride (1:1); L-Lysine, N6-(4-amino-1-β-D-ribofuranosyl-2(1H)-pyrimidinylidene)-, monohydrochloride; Lysidine (nucleoside); N6-(4-Amino-1-β-D-ribofuranosyl-2(1H)-pyrimidinylidene)-L-lysine hydrochloride

CAS

116120-47-9

IUPAC Name

(2S)-2-amino-6-[[4-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-ylidene]amino]hexanoic acid;hydrochloride

Molecular Weight

407.85

Molecular Formula

C15H25N5O6.HCl

Canonical SMILES

Cl.O=C(O)C(N)CCCCN=C1N=C(N)C=CN1C2OC(CO)C(O)C2O

InChI

InChI=1S/C15H25N5O6.ClH/c16-8(14(24)25)3-1-2-5-18-15-19-10(17)4-6-20(15)13-12(23)11(22)9(7-21)26-13;/h4,6,8-9,11-13,21-23H,1-3,5,7,16H2,(H,24,25)(H2,17,18,19);1H/t8-,9+,11+,12+,13+;/m0./s1

InChIKey

BTLJFKUMSPUPNB-ZGVNSRHASA-N

Purity

≥95%

Symbol

k²C

Chemical Structure:

Reference Reading

1. tRNA Modifications: Impact on Structure and Thermal Adaptation

Christian Lorenz, Christina E Lünse, Mario Mörl. Biomolecules. 2017 Apr 4;7(2):35. doi: 10.3390/biom7020035.

Transfer RNAs (tRNAs) are central players in translation, functioning as adapter molecules between the informational level of nucleic acids and the functional level of proteins. They show a highly conserved secondary and tertiary structure and the highest density of post-transcriptional modifications among all RNAs. These modifications concentrate in two hotspots-the anticodon loop and the tRNA core region, where the D- and T-loop interact with each other, stabilizing the overall structure of the molecule. These modifications can cause large rearrangements as well as local fine-tuning in the 3D structure of a tRNA. The highly conserved tRNA shape is crucial for the interaction with a variety of proteins and other RNA molecules, but also needs a certain flexibility for a correct interplay. In this context, it was shown that tRNA modifications are important for temperature adaptation in thermophilic as well as psychrophilic organisms, as they modulate rigidity and flexibility of the transcripts, respectively. Here, we give an overview on the impact of modifications on tRNA structure and their importance in thermal adaptation.

2. Discovery and characterization of tRNAIle lysidine synthetase (TilS)

Tsutomu Suzuki, Kenjyo Miyauchi. FEBS Lett. 2010 Jan 21;584(2):272-7. doi: 10.1016/j.febslet.2009.11.085.

In the bacterial decoding system, the AUA codon is deciphered as isoleucine by tRNA(Ile) bearing lysidine (L, 2-lysyl-cytidine) at the wobble position. Lysidine is an essential modification that determines both the codon and amino acid specificities of tRNA(Ile). We identified an enzyme named tRNA(Ile) lysidine synthetase (TilS) that catalyzes lysidine formation by using lysine and ATP as substrates. Biochemical studies revealed a molecular mechanism of lysidine formation that consists of two consecutive reactions involving the adenylated tRNA intermediate. In addition, we deciphered how Escherichia coli TilS specifically discriminates between tRNA(Ile) and the structurally similar tRNA(Met), which bears the same anticodon loop. Recent structural studies unveiled tRNA recognition by TilS, and a molecular basis of lysidine formation at atomic resolution.

3. Synthesis of a Protected keto-Lysidine Analogue via Improved Preparation of Arabino-isoCytosine Nucleosides

Joseph B Sweeney, Paul A Bethel, Duncan M Gill, Agata M Ochocińska, Anthony E J Walsh, Scarlett M Walton. Org Lett. 2019 Apr 5;21(7):2004-2007. doi: 10.1021/acs.orglett.9b00086.

Anhydrouridines react with aliphatic amines to give N-alkyl isocytosines, but reported procedures often demand very long reaction times and can be low yielding, with narrow scope. A modified procedure for such reactions has been developed, using microwave irradiation, significantly reducing reaction time and allowing facile access to a diverse range of novel nucleosides on the gram scale. The method has been used to prepare a precursor to a novel analogue of lysidine, a naturally occurring iminonucleoside found in tRNA.