Nα-Boc-Nω-(mesitylene-2-sulfonyl)-L-arginine
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Nα-Boc-Nω-(mesitylene-2-sulfonyl)-L-arginine

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Category
BOC-Amino Acids
Catalog number
BAT-002984
CAS number
136625-03-1
Molecular Formula
C20H32N4O6S
Molecular Weight
456.57
Nα-Boc-Nω-(mesitylene-2-sulfonyl)-L-arginine
IUPAC Name
(2S)-5-[[amino-[(2,4,6-trimethylphenyl)sulfonylamino]methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Synonyms
Boc-L-Arg(Mts)-OH; (2S)-5-[[amino-[(2,4,6-trimethylphenyl)sulfonylamino]methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.28 g/cm3
Storage
Store at-20 °C
InChI
InChI=1S/C20H32N4O6S/c1-12-10-13(2)16(14(3)11-12)31(28,29)24-18(21)22-9-7-8-15(17(25)26)23-19(27)30-20(4,5)6/h10-11,15H,7-9H2,1-6H3,(H,23,27)(H,25,26)(H3,21,22,24)/t15-/m0/s1
InChI Key
QXWQVNSGMVITAR-HNNXBMFYSA-N
Canonical SMILES
CC1=CC(=C(C(=C1)C)S(=O)(=O)NC(=NCCCC(C(=O)O)NC(=O)OC(C)(C)C)N)C

One of the key applications of Nα-Boc-Nω-(mesitylene-2-sulfonyl)-L-arginine is as a building block in peptide synthesis. This compound, often protected with the Boc (tert-butyloxycarbonyl) group, is useful for constructing more complex peptide chains due to its stability and reactivity. The mesitylene-2-sulfonyl group protects the guanidino functional group of arginine, preventing unwanted side reactions during synthesis. This protection allows for precise incorporation into growing peptide chains, making it invaluable in the development of synthetic peptides for research, pharmaceuticals, and biotechnology applications.

Another key application of Nα-Boc-Nω-(mesitylene-2-sulfonyl)-L-arginine is in the design and testing of enzyme inhibitors. Arginine residues often play critical roles in enzyme active sites, and by containing specific protecting groups, this compound allows researchers to study enzyme-substrate interactions in detail. This can lead to the development of specific inhibitors that can modulate enzyme activity, offering potential therapeutic benefits in conditions where enzyme regulation is crucial, such as in cancer, bacterial infections, and metabolic disorders.

Nα-Boc-Nω-(mesitylene-2-sulfonyl)-L-arginine can also be used in the study of protein-protein interactions. Due to the critical role of arginine in forming hydrogen bonds and salt bridges within protein structures, this protected form of arginine can be introduced into peptides or proteins to investigate their binding properties. This application is essential in structural biology and drug design, where understanding the detailed interactions at the molecular level can guide the development of molecules that can effectively disrupt or stabilize these interactions in a therapeutic context.

Furthermore, Nα-Boc-Nω-(mesitylene-2-sulfonyl)-L-arginine is valuable in the study of arginine-rich proteins and peptides. Arginine plays a significant role in the function and structure of various proteins due to its ability to interact with negatively charged molecules like DNA and phosphorylated proteins. By using a protected form of arginine, researchers can systematically modify and study the effects of arginine in these proteins and peptides. This understanding can provide insights into cellular processes such as signal transduction, gene regulation, and protein synthesis, ultimately leading to the development of new therapeutic strategies for diseases caused by dysregulation of these processes.

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