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

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Category
BOC-Amino Acids
Catalog number
BAT-002979
CAS number
200125-12-8
Molecular Formula
C25H40N4O7S
Molecular Weight
540.69
Nα-Boc-Nω-(2,2,4,6,7-pentamethylchroman-6-sufonyl)-L-arginine
IUPAC Name
(2S)-5-[[amino-[(2,2,5,7,8-pentamethyl-3,4-dihydrochromen-6-yl)sulfonylamino]methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Synonyms
Boc-L-Arg(Pmc)-OH; Nalpha-Boc-Nomega-(2,2,4,6,7-pentamethylchroman-6-sufonyl)-L-arginine; (S)-2-((tert-Butoxycarbonyl)amino)-5-(3-((2,2,5,7,8-pentamethylchroman-6-yl)sulfonyl)guanidino)pentanoic acid
Appearance
White to off-white powder
Purity
≥ 99% (HPLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C25H40N4O7S/c1-14-15(2)20(16(3)17-11-12-25(7,8)35-19(14)17)37(33,34)29-22(26)27-13-9-10-18(21(30)31)28-23(32)36-24(4,5)6/h18H,9-13H2,1-8H3,(H,28,32)(H,30,31)(H3,26,27,29)/t18-/m0/s1
InChI Key
WVNWVMLZWUTJPA-SFHVURJKSA-N
Canonical SMILES
CC1=C(C(=C(C2=C1OC(CC2)(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-pentamethylchroman-6-sulfonyl)-L-arginine, a versatile compound commonly known as a protected amino acid derivative, finds diverse applications in both biochemical and pharmaceutical realms. Here are the key applications of Nα-Boc-Nω-(2,2,4,6,7-pentamethylchroman-6-sulfonyl)-L-arginine presented with a high degree of perplexity and burstiness:

Peptide Synthesis: Serving as a pivotal component in peptide synthesis, Nα-Boc-Nω-(2,2,4,6,7-pentamethylchroman-6-sulfonyl)-L-arginine acts as a foundational building block. Its intricate structure, equipped with bulky groups and protective elements, facilitates precise reactions and shields against undesired side interactions throughout the synthesis process. This attribute renders it invaluable for generating peptides of exceptional purity, essential for both research endeavors and therapeutic applications.

Drug Development: Within the realm of pharmaceutical exploration, this compound plays a crucial role in producing arginine-containing analogues and derivatives. These modified compounds undergo scrutiny for their biological activities and therapeutic potentials. By manipulating the characteristics of the arginine component, researchers can fine-tune drug candidates to enhance efficacy and minimize adverse effects, propelling advancements in drug development and medical treatment.

Enzyme Inhibition Studies: Researchers harness the capabilities of Nα-Boc-Nω-(2,2,4,6,7-pentamethylchroman-6-sulfonyl)-L-arginine as a powerful tool for delving into enzyme-substrate interactions. Its tailored modifications make it an ideal candidate for dissecting the specificity and mechanisms of enzymes targeting arginine residues. Through these investigations, valuable insights into enzyme functionalities are unveiled, offering potential avenues for therapeutic interventions and deepening the understanding of enzymatic processes.

Proteomics Research: In the domain of proteomics, this derivative emerges as a valuable asset for synthesizing tagged peptides crucial for mass spectrometry-based analyses. The distinctive structure of Nα-Boc-Nω-(2,2,4,6,7-pentamethylchroman-6-sulfonyl)-L-arginine enables enhanced detection and quantification of peptides, elevating the precision of protein identification and characterization within complex biological samples. This application amplifies the accuracy and depth of proteomic investigations, opening new vistas for deciphering intricate protein landscapes.

1. 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.
2. 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.
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