Nα-Fmoc-Nω-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-D-arginine
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Nα-Fmoc-Nω-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-D-arginine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003711
CAS number
120075-24-3
Molecular Formula
C31H36N4O7S
Molecular Weight
608.90
Nα-Fmoc-Nω-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-D-arginine
IUPAC Name
(2R)-5-[[amino-[(4-methoxy-2,3,6-trimethylphenyl)sulfonylamino]methylidene]amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid
Synonyms
Fmoc-D-Arg(Mtr)-OH; N-Fmoc-N'-(4-Methoxy-2,3,6-Trimethylbenzenesulfonyl)-D-Arginine
Purity
≥ 99% (HPLC)
Density
1.35±0.1 g/cm3(Predicted)
Melting Point
123-130 °C
Boiling Point
807.776°C at 760 mmHg
Storage
Store at 2-8°C
InChI
InChI=1S/C31H36N4O7S/c1-18-16-27(41-4)19(2)20(3)28(18)43(39,40)35-30(32)33-15-9-14-26(29(36)37)34-31(38)42-17-25-23-12-7-5-10-21(23)22-11-6-8-13-24(22)25/h5-8,10-13,16,25-26H,9,14-15,17H2,1-4H3,(H,34,38)(H,36,37)(H3,32,33,35)/t26-/m1/s1
InChI Key
LKGHIEITYHYVED-AREMUKBSSA-N
Canonical SMILES
CC1=CC(=C(C(=C1S(=O)(=O)NC(=NCCCC(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24)N)C)C)OC

Nα-Fmoc-Nω-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-D-arginine, a specialized reagent crucial in peptide synthesis and biochemistry research, finds diverse applications in the scientific realm.

Peptide Synthesis: Integral to solid-phase peptide synthesis (SPPS), this compound acts as a shielded amino acid. With its Fmoc group allowing for selective deprotection, it facilitates the meticulous assembly of peptides. Its role is paramount in generating peptides of exceptional purity for both research endeavors and therapeutic pursuits.

Bioconjugation: Nα-Fmoc-Nω-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-D-arginine serves a pivotal role in bioconjugation reactions, acting as a foundational element to connect peptides with various biomolecules. This function is particularly advantageous in crafting peptide-based probes, affinity tags, and conjugate vaccines, thanks to its specific sulfonyl protection group that ensures precise and systematic conjugation activities.

Protease Inhibition Studies: In biochemical assessments, this compound becomes a valuable tool for probing the mechanisms underlying protease function and inhibition. Researchers leverage it to assess the specificity and efficacy of proteolytic enzymes when interacting with peptides containing this modified arginine, a critical step in identifying potential protease inhibitors as viable therapeutic interventions.

Drug Development: Beyond its exploratory applications, this compound contributes significantly to the design of novel therapeutic peptides and peptidomimetics. By incorporating Nα-Fmoc-Nω-(4-methoxy-2,3,6-trimethylbenzenesulfonyl)-D-arginine into these entities, researchers can improve their stability, bioavailability, and target specificity. These are essential elements in the creation of advanced medicinal compounds with enhanced therapeutic efficacy and safety profiles.

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