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

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Fmoc-N-Me-Arg(pbf)-OH is a peptide used in the preparation of tetrapeptide aldehyde inhibitors of dengue virus NS3 protease.

Category
Fmoc-Amino Acids
Catalog number
BAT-007733
CAS number
913733-27-4
Molecular Formula
C35H42N4O7S
Molecular Weight
662.80
Nα-Fmoc-Nα-methyl-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-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]pentanoic acid
Synonyms
Fmoc-N-Me-L-Arg(Pbf)-OH; N5-[[[(2,3-dihydro-2,2,4,6,7-pentamethyl-5-benzofuranyl)sulfonyl]amino]iminomethyl]-N2-[(9H-fluoren-9-ylmethoxy)carbonyl]-N2-methyl-L-Ornithine; FMOC-MEARG(PBF)-OH; N-alpha-(9-Fluorenylmethoxycarbonyl)-N-alpha-methyl-N-omega-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine; (2S)-5-[[amino-[(2,2,4,6,7-pentamethyl-3H-1-benzofuran-5-yl)sulfonylamino]methylidene]amino]-2-[9H-fluoren-9-ylmethoxycarbonyl(methyl)amino]pentanoic acid
Appearance
White to off-white powder
Purity
≥ 99.5% (Chiral HPLC)
Density
1.340±0.10 g/cm3 (Predicted)
Boiling Point
817.5±75.0 °C (Predicted)
Storage
Store at 2-8 °C
InChI
InChI=1S/C35H42N4O7S/c1-20-21(2)31(22(3)27-18-35(4,5)46-30(20)27)47(43,44)38-33(36)37-17-11-16-29(32(40)41)39(6)34(42)45-19-28-25-14-9-7-12-23(25)24-13-8-10-15-26(24)28/h7-10,12-15,28-29H,11,16-19H2,1-6H3,(H,40,41)(H3,36,37,38)/t29-/m0/s1
InChI Key
MEGKXARLCPKZHJ-LJAQVGFWSA-N
Canonical SMILES
CC1=C(C(=C(C2=C1OC(C2)(C)C)C)S(=O)(=O)NC(=NCCCC(C(=O)O)N(C)C(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)N)C

Nα-Fmoc-Nα-methyl-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine, a highly specialized reagent, finds application in peptide synthesis and diverse biochemical research realms. Here are the key applications:

Peptide Synthesis: Serving as a derivative of L-arginine, this compound plays a vital role in the solid-phase construction of peptides, enabling precise control over the synthesis process. This meticulous approach ensures the production of highly pure peptides with exceptional yields. It is instrumental in the creation of peptides with intricate sequences, crucial for pharmaceutical research and the development of therapeutic agents.

Proteomics Research: Within the realm of proteomics, this unique compound proves invaluable for studying protein-protein interactions and post-translational modifications. By integrating into synthetic peptides, it facilitates the creation of probes or standards used in mass spectrometry-based proteomics. This methodology aids in the identification and quantification of proteins within complex biological samples, advancing our comprehension of cellular processes at a fundamental level.

Drug Development: Playing a pivotal role in drug design, Nα-Fmoc-Nα-methyl-Nω-(2,2,4,6,7-pentamethyldihydrobenzofuran-5-sulfonyl)-L-arginine possesses specific chemical attributes ideal for crafting peptide-based therapeutic interventions. These peptides can serve as potent inhibitors or activators of biological targets, holding immense potential for novel therapeutic strategies targeting diseases such as cancer, diabetes, and autoimmune conditions.

Biochemical Assays: This specialized arginine derivative is a cornerstone in various biochemical assays aimed at exploring enzyme activity and substrate specificity. Its utilization aids in the creation and validation of assays crucial for measuring the activities of arginine-modifying enzymes like arginases and nitric oxide synthases. Such assays are essential for deciphering enzyme functions and play a pivotal role in drug discovery endeavors focused on these enzyme targets.

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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