Fmoc-L-glutamine
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Fmoc-L-glutamine

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N2-Fmoc-L-glutamine is an N-Fmoc-protected form of L-Glutamine. L-Glutamine is a non-essential amino acid that is important for cells which proliferate quickly in the body, such as those of the immune system. L-Glutamine is known to be especially important for the gut, as it helps maintain intestinal structure and function. L-Glutamine also has protective properties against host toxicity of chemotherapy in cancer patients.

Category
Fmoc-Amino Acids
Catalog number
BAT-003764
CAS number
71989-20-3
Molecular Formula
C20H20N2O5
Molecular Weight
368.40
Fmoc-L-glutamine
IUPAC Name
(2S)-5-amino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoic acid
Synonyms
Fmoc-L-glutamine; NA-FMOC-L-GLUTAMINE; FMOC-GLN; FMOC-L-GLN; L-GLUTAMINE-N-FMOC; FMOC-L-GLN-OH; Fmoc-Glutamine-OH; FMOC-GLUTAMINE; Fmoc-D-Gln-OH
Appearance
White powder
Purity
≥ 99% (HPLC, Chiral purity)
Density
1.332 g/cm3
Melting Point
208-222 °C
Boiling Point
498.7 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C20H20N2O5/c21-18(23)10-9-17(19(24)25)22-20(26)27-11-16-14-7-3-1-5-12(14)13-6-2-4-8-15(13)16/h1-8,16-17H,9-11H2,(H2,21,23)(H,22,26)(H,24,25)/t17-/m0/s1
InChI Key
IZKGGDFLLNVXNZ-KRWDZBQOSA-N
Canonical SMILES
C1=CC=C2C(=C1)C(C3=CC=CC=C32)COC(=O)NC(CCC(=O)N)C(=O)O

Fmoc-L-glutamine, a versatile protected amino acid used extensively in peptide synthesis and research, showcases a diverse range of applications. Here are four key applications of Fmoc-L-glutamine:

Peptide Synthesis: Deeply embedded in solid-phase peptide synthesis, Fmoc-L-glutamine plays a critical role in safeguarding against unwanted side reactions, ensuring the smooth progression of chain elongation. With its Fmoc protecting group strategically deployed, this amino acid effectively prevents undesired reactions, facilitating the precise formation of peptide bonds. Researchers harness the power of Fmoc-L-glutamine to intricately craft peptides with complex sequences.

Protein Engineering: Positioned at the forefront of protein engineering, Fmoc-L-glutamine emerges as a foundational element for enhancing protein stability, activity, or specificity. By seamlessly incorporating this amino acid into protein structures, scientists venture into uncharted territories of novel enzyme functions and tailor-made therapeutics for enhanced efficacy. This strategic integration assists in customizing proteins for industrial applications and driving forward the development of pharmaceutical agents with superior performance capabilities.

Bioconjugation Studies: Carving its path in bioconjugation methodologies, Fmoc-L-glutamine facilitates the coupling of proteins or peptides with a diverse array of molecules, such as drugs or imaging agents. Its strategic inclusion ensures that the glutamine side chain remains easily accessible for conjugation, fostering the creation of multifunctional compounds. This capability serves as a cornerstone in the development of targeted therapies and diagnostic tools, fueling progress in precision medicine and innovative therapeutic modalities.

Biological Research: Within the realm of biological research, Fmoc-L-glutamine assumes a central and indispensable role in biochemical assays, unraveling intricate protein-protein interactions and cellular processes intricately linked to glutamine. By seamlessly integrating into peptides, researchers decode the complexities of glutamine's involvement in cellular signaling and metabolic pathways.

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