Fmoc-Gln-OH (CAS: 118609-68-0) represents a vital molecule in the toolkit of modern synthetic chemists, particularly those engaged in peptide synthesis. Its importance stems from the synergy between the Fmoc protecting group and the L-glutamine amino acid residue, facilitating precise peptide chain elongation. Understanding its chemical nature is key to leveraging its full potential.

At its core, Fmoc-Gln-OH is a derivative of the naturally occurring amino acid L-glutamine. The L-glutamine residue features an amide-containing side chain, which contributes to the peptide's polarity and potential for hydrogen bonding. The 'Fmoc' prefix denotes the attachment of the 9-fluorenylmethyloxycarbonyl group to the alpha-amino nitrogen. This bulky, base-labile protecting group is instrumental in solid-phase peptide synthesis (SPPS). The Fmoc group shields the amine functionality during coupling reactions with the activated carboxyl terminus of the growing peptide chain. Its removal, typically achieved using a dilute solution of piperidine, regenerates the free amine, ready for the next amino acid coupling step.

The chemical identity of Fmoc-Gln-OH is precisely defined by its molecular formula, C20H20N2O5, and a molecular weight of approximately 368.383 g/mol. These parameters are fundamental for accurate stoichiometric calculations in synthesis protocols. The purity of the compound is of utmost importance; impurities can lead to incomplete reactions, resulting in truncated peptide sequences or undesired side products, which complicates downstream purification efforts and reduces overall yield.

The significance of Fmoc-Gln-OH in synthesis lies in the Fmoc strategy's advantages: mild deprotection conditions that preserve acid-labile protecting groups on side chains and peptide anchors, and the ability to monitor deprotection progress spectrophotometrically due to the Fmoc group's UV absorbance. This makes it a preferred choice for synthesizing sensitive or complex peptides.

Applications of Fmoc-Gln-OH extend beyond basic peptide synthesis. It is a crucial intermediate for:

  • Therapeutic Peptide Development: Synthesizing peptide drugs often requires precise incorporation of specific amino acids like glutamine.
  • Peptide Libraries: Creating diverse peptide libraries for screening biological activity or identifying lead compounds.
  • Bioconjugation: Preparing peptides for subsequent conjugation to other molecules like labels or carriers.

When sourcing Fmoc-Gln-OH (CAS 118609-68-0), researchers and manufacturers should always look for high purity and comprehensive documentation from their suppliers. Engaging with manufacturers who can provide consistent quality, often at competitive prices, ensures the reliability of synthetic outcomes. Whether for academic research or industrial production, understanding the chemistry of this essential building block is fundamental to success.