Nα-Boc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sufonyl)-L-arginine
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Nα-Boc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sufonyl)-L-arginine

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Category
BOC-Amino Acids
Catalog number
BAT-002980
CAS number
200124-22-7
Molecular Formula
C24H38N4O7S
Molecular Weight
526.77
Nα-Boc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sufonyl)-L-arginine
IUPAC Name
(2S)-5-[[amino-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Synonyms
Boc-L-Arg(Pbf)-OH; (S)-2-((tert-Butoxycarbonyl)amino)-5-(3-((2,2,4,6,7-pentamethyl-2,3-dihydrobenzofuran-5-yl)sulfonyl)guanidino)pentanoic acid
Appearance
White powder
Purity
≥ 98% (HPLC)
Density
1.31±0.1 g/cm3(Predicted)
Melting Point
71-92 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C24H38N4O7S/c1-13-14(2)19(15(3)16-12-24(7,8)34-18(13)16)36(32,33)28-21(25)26-11-9-10-17(20(29)30)27-22(31)35-23(4,5)6/h17H,9-12H2,1-8H3,(H,27,31)(H,29,30)(H3,25,26,28)/t17-/m0/s1
InChI Key
CVFXPOKENLGCID-KRWDZBQOSA-N
Canonical SMILES
CC1=C(C(=C(C2=C1OC(C2)(C)C)C)S(=O)(=O)NC(=NCCCC(C(=O)O)NC(=O)OC(C)(C)C)N)C

Nα-Boc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine, a synthetic compound with specific applications in bioorganic and medicinal chemistry, boasts a diverse array of uses. Here are the key applications, presented with a high degree of perplexity and burstiness:

Protease Inhibitor Studies: Acting as a selective inhibitor, this compound serves as a valuable tool in the intricate realm of protease research. Proteases, pivotal players in numerous physiological processes and diseases, are the focus of intense scrutiny. By pinpointing specific proteases for inhibition, researchers unravel the biological intricacies of these enzymes, shedding light on their therapeutic potential. This wealth of knowledge fuels the development of cutting-edge pharmaceuticals targeting conditions ranging from cancer to inflammatory diseases.

Peptide Synthesis: Delving into the realm of solid-phase peptide synthesis, Nα-Boc-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine shines as a protected amino acid derivative. The Boc group, a safeguard for the amino group during synthesis, ensures precise peptide assembly. This precision is paramount in crafting bespoke peptides for research and therapeutic endeavors, unlocking new frontiers in peptide-based applications.

Structural Biology: In the intricate landscape of structural biology, this compound emerges as a potent tool for probing protein-ligand interactions through advanced techniques like X-ray crystallography and NMR spectroscopy. By binding to specific sites on target proteins, it unravels the three-dimensional tapestry and functional dynamics of biomolecules, fueling drug discovery and offering unprecedented insights into molecular mechanisms at play.

Signal Transduction Research: Engaging in the exploration of signal transduction pathways, this compound unravels the intricate dance of cellular responses to diverse stimuli. Through the selective modification of arginine residues within proteins, researchers dissect the roles of these key residues in cellular signaling pathways. This meticulous inquiry unveils novel signaling cascades and potential therapeutic avenues, pushing the boundaries of signal transduction research to new heights.

1. Synthesis of a non-peptidic PET tracer designed for α5β1 integrin receptor
Alessandra Monaco, Olivier Michelin, John Prior, Curzio Rüegg, Leonardo Scapozza, Yann Seimbille J Labelled Comp Radiopharm. 2014 May 15;57(5):365-70. doi: 10.1002/jlcr.3190. Epub 2014 Mar 14.
Arginine-glycine-aspartic acid (RGD)-containing peptides have been traditionally used as PET probes to noninvasively image angiogenesis, but recently, small selective molecules for α5 β1 integrin receptor have been developed with promising results. Sixty-one antagonists were screened, and tert-butyl (S)-3-(2-((3R,5S)-1-(3-(1-(2-fluoroethyl)-1H-1,2,3-triazol-4-yl)propanoyl)-5-((pyridin-2-ylamino)methyl)pyrrolidin-3-yloxy)acetamido)-2-(2,4,6-trimethylbenzamido)propanoate (FPMt) was selected for the development of a PET tracer to image the expression of α5 β1 integrin receptors. An alkynyl precursor (PMt) was initially synthesized in six steps, and its radiolabeling was performed according to the azide-alkyne copper(II)-catalyzed Huisgen's cycloaddition by using 1-azido-2-[(18)F]fluoroethane ([(18)F]12). Different reaction conditions between PMt and [(18)F]12 were investigated, but all of them afforded [(18)F]FPMt in 15 min with similar radiochemical yields (80-83%, decay corrected). Overall, the final radiopharmaceutical ([(18)F]FPMt) was obtained after a synthesis time of 60-70 min in 42-44% decay-corrected radiochemical yield.
2. 1,2-Dimethylindole-3-sulfonyl (MIS) as protecting group for the side chain of arginine
Albert Isidro, Daniel Latassa, Matthieu Giraud, Mercedes Alvarez, Fernando Albericio Org Biomol Chem. 2009 Jun 21;7(12):2565-9. doi: 10.1039/b904836g. Epub 2009 Apr 23.
The protection of arginine (Arg) side chains is a crucial issue in peptide chemistry because of the propensity of the basic guanidinium group to produce side reactions. Currently, sulfonyl-type protecting groups, such as 2,2,5,7,8-pentamethylchroman (Pmc) and 2,2,4,6,7-pentamethyldihydrobenzofurane (Pbf), are the most widely used for this purpose. Nevertheless, Arg side chain protection remains problematic as a result of the acid stability of these two compounds. This issue is even more relevant in Arg-rich sequences, acid-sensitive peptides and large-scale syntheses. The 1,2-dimethylindole-3-sulfonyl (MIS) group is more acid-labile than Pmc and Pbf and can therefore be a better option for Arg side chain protection. In addition, MIS is compatible with tryptophan-containing peptides.
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