n2-Isobutyrylguanosine monohydrate

• CAS: 64350-24-9
• Catalog Number: ACM64350249
• Category: Main Products
• Molecular Weight: 353.33
• Molecular Formula: C₁₄H₁₉N₅O₆
• Synonyms: N2-ISOBUTYRYL GUANOSINE
• IUPAC Name: N-Isobutyrylguanosine
• Melting Point: 148ºC
• Density: 1.82 g/cm³
• Appearance: White to off-white powder
• Exact Mass: 353.13400

Case Study

N2-Isobutyrylguanosine: Enabling High-Purity mRNA Therapeutics through Advanced Cap Analog Design

Abe, Hiroshi, et al. (2024). [DOI: 10.21203/rs.3.rs-2119525/v1]

In this work, N2-Isobutyrylguanosine served as a practical phosphorylation precursor in the synthesis of hydrophobic, photocleavable cap analogs (PureCap), enabling RP-HPLC purification of fully capped mRNA with 100% capping efficiency and markedly improved translation.
Approach: Removing immunogenic uncapped (5' ppp) RNA from IVT mRNA is essential but difficult because capped and uncapped species share similar physicochemical properties. The study introduced hydrophobic, photocaged cap analogs that integrate into the 5' terminus during IVT so capped mRNA can be separated by reversed-phase HPLC and then restored to a native cap by light irradiation. N2-Isobutyrylguanosine was used as the starting nucleoside for preparing a 2'-O-nitrobenzyl (Nb)-modified guanosine precursor via a four-step sequence: TIPDS protection (quantitative), Nb installation (product 13, 76% yield), silyl deprotection (75% yield), and isobutyryl removal with 28% aqueous ammonia to give the 2'-O-Nb guanosine (70% yield). These documented steps enabled clean access to the diphosphate intermediates required for PureCap analog assembly.
Results: The PureCap workflow produced footprint-free, fully capped mRNA (reported 100% capping efficiency) and allowed preparation of Cap-2 mRNA that showed up to 3-4× higher translation activity versus conventional Cap-1 mRNA.

Custom Q&A

What is the molecular formula of n2-Isobutyrylguanosine monohydrate?

The molecular formula is C14H21N5O7.

What are the synonyms for n2-Isobutyrylguanosine monohydrate?

The synonyms are n2-isobutyrylguanosine monohydrate and N-Isobutyrylguanosine hydrate.

What is the IUPAC name of n2-Isobutyrylguanosine monohydrate?

The IUPAC name is N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-oxo-1H-purin-2-yl]-2-methylpropanamide;hydrate.

What is the InChI of n2-Isobutyrylguanosine monohydrate?

The InChI is InChI=1S/C14H19N5O6.H2O/c1-5(2)11(23)17-14-16-10-7(12(24)18-14)15-4-19(10)13-9(22)8(21)6(3-20)25-13;/h4-6,8-9,13,20-22H,3H2,1-2H3,(H2,16,17,18,23,24);1H2/t6-,8-,9-,13-;/m1./s1.

What is the InChIKey of n2-Isobutyrylguanosine monohydrate?

The InChIKey is JXIMAIWXKDBJKP-DOKXERMVSA-N.

What is the canonical SMILES of n2-Isobutyrylguanosine monohydrate?

The canonical SMILES is CC(C)C(=O)NC1=NC2=C(C(=O)N1)N=CN2C3C(C(C(O3)CO)O)O.O.

What is the molecular weight of n2-Isobutyrylguanosine monohydrate?

The molecular weight is 371.35g/mol.

How many hydrogen bond donor counts does n2-Isobutyrylguanosine monohydrate have?

It has 6 hydrogen bond donor counts.

How many hydrogen bond acceptor counts does n2-Isobutyrylguanosine monohydrate have?

It has 9 hydrogen bond acceptor counts.

How many rotatable bond counts does n2-Isobutyrylguanosine monohydrate have?

It has 4 rotatable bond counts.