Nα-Boc-Nγ-xanthyl-L-asparagine
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Nα-Boc-Nγ-xanthyl-L-asparagine

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Category
BOC-Amino Acids
Catalog number
BAT-002964
CAS number
65420-40-8
Molecular Formula
C22H24N2O6
Molecular Weight
412.40
Nα-Boc-Nγ-xanthyl-L-asparagine
IUPAC Name
(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxo-4-(9H-xanthen-9-ylamino)butanoic acid
Synonyms
Boc-L-Asn(Xan)-OH; N-Alpha-t-Boc-N-beta-xanthyl-L-asparagine; N-Boc-N-xanthyl-L-asparagine
Appearance
Off-white powder
Purity
≥ 99.9% (Chiral HPLC)
Density
1.32±0.1 g/cm3(Predicted)
Melting Point
173-175 °C
Boiling Point
650.7±55.0 °C(Predicted)
Storage
Store at 2-8°C
InChI
InChI=1S/C22H24N2O6/c1-22(2,3)30-21(28)23-15(20(26)27)12-18(25)24-19-13-8-4-6-10-16(13)29-17-11-7-5-9-14(17)19/h4-11,15,19H,12H2,1-3H3,(H,23,28)(H,24,25)(H,26,27)/t15-/m0/s1
InChI Key
YMGDQLXBNMRJMR-HNNXBMFYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CC(=O)NC1C2=CC=CC=C2OC3=CC=CC=C13)C(=O)O

Nα-Boc-Nγ-xanthyl-L-asparagine, a derivative of the amino acid asparagine, finds diverse applications in research and biochemistry.

Peptide Synthesis: Serving as a fundamental component in solid-phase peptide synthesis, Nα-Boc-Nγ-xanthyl-L-asparagine plays a pivotal role as a protected building block. The Boc (tert-butyloxycarbonyl) group shields the amine functionality, whereas the xanthyl group guards the side chain, enabling selective deprotection. This intricate process facilitates the creation of intricate peptides with unparalleled precision and purity.

Drug Development: Within the realm of pharmaceutical research, Nα-Boc-Nγ-xanthyl-L-asparagine is a cornerstone in the design and synthesis of peptide-based drug candidates. The compound’s protected form ensures stability throughout the drug development lifecycle, fostering the synthesis of therapeutic peptides with tailored biological activities. This precision is essential for crafting drugs that exhibit heightened efficacy and minimal adverse effects.

Proteomics Studies: Renowned for its utility in proteomics, Nα-Boc-Nγ-xanthyl-L-asparagine is instrumental in exploring protein-protein interactions and post-translational modifications. By incorporating this safeguarded amino acid into synthetic peptides, researchers can identify critical modifications like phosphorylation and glycosylation. This comprehensive approach enhances comprehension of protein functions and interactions within intricate biological systems.

Bioconjugation: Noteworthy for its versatility, the protected groups present on Nα-Boc-Nγ-xanthyl-L-asparagine make it an exceptional option for bioconjugation procedures. This amino acid derivative can be conjugated to various molecules, such as fluorophores or drugs, to generate conjugates for diverse applications in imaging, targeting, or therapeutics. This adaptability amplifies the efficacy of bioconjugated molecules in diagnostics and targeted drug delivery systems.

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