N-α-(9-Fluorenylmethoxycarbonyl)-N-ω1,N-δ-di(t-butoxycarbonyl)-L-arginine
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N-α-(9-Fluorenylmethoxycarbonyl)-N-ω1,N-δ-di(t-butoxycarbonyl)-L-arginine

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Category
Fmoc-Amino Acids
Catalog number
BAT-001780
CAS number
158899-11-7
Molecular Formula
C31H40N4O8
Molecular Weight
596.69
IUPAC Name
(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxycarbonyl-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]amino]pentanoic acid
Synonyms
Fmoc-Arg(Boc)2-OH; N-alpha-(9-Fluorenylmethoxycarbonyl)-N-omega1,N-delta-di(t-butoxycarbonyl)-L-arginine
Storage
Store at -20 °C
InChI
InChI=1S/C31H40N4O8/c1-30(2,3)42-28(39)34-26(32)35(29(40)43-31(4,5)6)17-11-16-24(25(36)37)33-27(38)41-18-23-21-14-9-7-12-19(21)20-13-8-10-15-22(20)23/h7-10,12-15,23-24H,11,16-18H2,1-6H3,(H,33,38)(H,36,37)(H2,32,34,39)/t24-/m0/s1
InChI Key
QAWFIDADTYJUPT-DEOSSOPVSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(=N)N(CCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C(=O)OC(C)(C)C

N-α-(9-Fluorenylmethoxycarbonyl)-N-ω1,N-δ-di(t-butoxycarbonyl)-L-arginine, a chemically-protected amino acid derivative crucial for peptide synthesis, finds diverse applications in the following areas expressed with high perplexity and burstiness:

Solid-Phase Peptide Synthesis: Embedded in the Fmoc solid-phase peptide synthesis methodology, this compound plays an irreplaceable role as a shielded version of L-arginine, enabling the sequential integration of amino acids while thwarting undesired side reactions. The strategic removal of protective groups promotes the streamlined assembly of intricate peptides, enhancing the method’s efficiency and versatility.

Drug Development: In the realm of pharmaceutical innovation, this compound emerges as a pivotal component for fabricating peptide-based drug contenders, particularly those earmarked for combating ailments such as cancer, diabetes, and neurodegenerative conditions. Leveraging shielded arginine derivatives, scientists fashion peptides imbued with heightened stability and bioactivity, ensuring their therapeutic potential remains unscathed throughout the drug development journey.

Bioconjugation: Embraced in bioconjugation practices, this compound facilitates the coupling of peptides with various biomolecules like antibodies, enzymes, or nanoparticles, birthing multifaceted bioconjugates tailored for targeted drug delivery or diagnostic imaging purposes. The safeguarded arginine side chains, meticulously preserved during conjugation, uphold the optimal functionality of the ultimate product, underscoring its critical role in creating versatile bioconjugates.

Protein Engineering: Empowering the construction of personalized proteins endowed with site-specific modifications, this compound emerges as a linchpin in protein engineering pursuits. By integrating shielded arginine into protein sequences, researchers orchestrate specific alterations, probing their impacts on protein functionality and resilience. This process lies at the heart of fashioning innovative proteins endowed with enhanced attributes poised for industrial or therapeutic deployment.

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