Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydro-benzofuran-5-sulfonyl)-L-arginine
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Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydro-benzofuran-5-sulfonyl)-L-arginine

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Category
Fmoc-Amino Acids
Catalog number
BAT-003708
CAS number
154445-77-9
Molecular Formula
C34H40N4O7S
Molecular Weight
648.77
Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydro-benzofuran-5-sulfonyl)-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-ylmethoxycarbonylamino)pentanoic acid
Synonyms
Fmoc-L-Arg(Pbf)-OH; (S)-2-((((9H-Fluoren-9-Yl)Methoxy)Carbonyl)Amino)-5-(3-((2,2,4,6,7-Pentamethyl-2,3-Dihydrobenzofuran-5-Yl)Sulfonyl)Guanidino)Pentanoic Acid; Nalpha-Fmoc-Nomega-Pbf-L-Arginine
Appearance
White to off-white powder
Purity
≥ 99.9% (Chiral HPLC)
Density
1.37±0.1 g/cm3(Predicted)
Melting Point
132 °C (dec)
Storage
Store at 2-8°C
InChI
InChI=1S/C34H40N4O7S/c1-19-20(2)30(21(3)26-17-34(4,5)45-29(19)26)46(42,43)38-32(35)36-16-10-15-28(31(39)40)37-33(41)44-18-27-24-13-8-6-11-22(24)23-12-7-9-14-25(23)27/h6-9,11-14,27-28H,10,15-18H2,1-5H3,(H,37,41)(H,39,40)(H3,35,36,38)/t28-/m0/s1
InChI Key
HNICLNKVURBTKV-NDEPHWFRSA-N
Canonical SMILES
CC1=C2C(=C(C(=C1C)S(=O)(=O)NC(=NCCCC(C(=O)O)NC(=O)OCC3C4=CC=CC=C4C5=CC=CC=C35)N)C)CC(O2)(C)C

Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydro-benzofuran-5-sulfonyl)-L-arginine, a specialized reagent with diverse biochemical and pharmaceutical applications, serves as a cornerstone in various scientific disciplines. Here are the key applications:

Peptide Synthesis: Positioned at the forefront of peptide synthesis, this compound acts as a protective shield for arginine residues during solid-phase peptide assembly. By safeguarding the arginine side chain, it shields against unwanted side reactions, ensuring the synthesis of meticulously purified peptides for both research and therapeutic endeavors.

Protein Modification: In the intricate realm of protein chemistry, this reagent plays a pivotal role in modifying and safeguarding specific amino acid residues within proteins or peptides. These modifications are essential for elucidating protein structure, function, and interactions, empowering researchers to craft tailor-made proteins and peptides with distinct characteristics.

Enzyme Inhibition Studies: Delving into enzyme mechanisms, Nα-Fmoc-Nω-(2,2,4,6,7-pentamethyldihydro-benzofuran-5-sulfonyl)-L-arginine emerges as a valuable tool for inhibiting enzymes that engage with arginine. By dissecting the repercussions of inhibition, researchers glean insights into enzyme functionality, paving the way for the development of potential therapeutic inhibitors. This pursuit fuels the exploration of novel drugs targeting specific enzymes, driving innovation in the pharmaceutical landscape.

Drug Development: At the forefront of drug discovery, this compound shines particularly in the inception stages of drug design and synthesis, where arginine-mimicking drugs come to life. Armed with this reagent, pharmaceutical chemists fashion compounds that closely mimic or interact with biological systems involving arginine, optimizing the potential for developing drugs with enhanced efficacy and diminished side effects.

1.Synthesis and pharmacological evaluation of new biphenylic derivatives as CB2 receptor ligands.
Bertini S1, Chicca A2, Arena C3, Chicca S2, Saccomanni G4, Gertsch J2, Manera C4, Macchia M4. Eur J Med Chem. 2016 Mar 30;116:252-266. doi: 10.1016/j.ejmech.2016.03.072. [Epub ahead of print]
Targeting type-2 cannabinoid receptor (CB2) is considered a feasible strategy to develop new drugs for the treatment of diseases like neuropathic pain, chronic inflammation, neurodegenerative disorders and cancer. Such drugs are devoid of the undesired central side effects that are typically mediated by the CB1 receptor. In this work we synthesized 18 biphenylic carboxamides as new CB2-selective ligands and evaluated their pharmacological profiles. The functional activity of these compounds is strongly influenced by the nature of the substituent at position 4' and 5 of the biphenyl scaffold. Position 5 seems to be responsible for the agonist or inverse agonist behaviour independently of the substituent in position 4', with the exception of the methoxyl group which transforms both full agonists and inverse agonists into neutral antagonists. This study provides a novel complete toolbox of CB2 functional modulators that derive from the same chemical scaffold.
2.Assessment of Sleep Quality and Effects of Relaxation Exercise on Sleep Quality in Patients Hospitalized in Internal Medicine Services in a University Hospital: The Effect of Relaxation Exercises in Patients Hospitalized.
Alparslan GB1, Orsal Ö, Unsal A. Holist Nurs Pract. 2016 May-Jun;30(3):155-165.
This study aims to assess sleep quality and determine the effects of relaxation exercise on sleep quality in patients hospitalized in internal medicine services. In total, 47 patients comprised the control group and did not engage in the exercise intervention-the progressive muscle relaxation exercise, whereas 235 patients were assigned to the intervention group (N = 282). In this study, Description Questionnaire Form and the Pittsburg Sleep Quality Index (PSQI) were used. Most patients (73.8%) had poor sleep quality. The mean pre- and postexercise PSQI scores of the patients in the interventional group were 8.7 ± 4.0 and 6.1 ± 3.3, respectively. The mean pre- and postexercise PSQI scores of the control patients were 6.6 ± 3.5 and 5.6 ± 2.7, respectively. According to this study, the exercises significantly enhanced the quality of sleep. Patients should be encouraged by nurses to perform relaxation exercises.
3.Migraine in Assiut Governorate, Egypt: epidemiology, risk factors, comorbid conditions and predictors of change from episodic to chronic migraine.
Kandil MR1, Hamed SA1, Fadel KA2, Khalifa HE1, Ghanem MK1, Mohamed KO1. Neurol Res. 2016 Mar 28:1-10. [Epub ahead of print]
OBJECTIVES: Headache is one of the most common complaints in medicine. Epidemiological and population-based studies reported that migraine has a variable prevalence worldwide. This study was done to estimate the prevalence of migraine across various age groups in Assiut district, Egypt.
4.Contribution of capsaicin-sensitive primary afferents to mechanical hyperalgesia induced by ventral root transection in rats: the possible role of BDNF.
Li W1, Wang JX1, Zhou ZH1, Lu Y1, Li XQ1, Liu BJ2, Chen HS1. Neurol Res. 2016 Feb 18:1-6. [Epub ahead of print]
OBJECTIVE: A recent study showed that brain-derived neurotrophic factor (BDNF) may play a role in the development of the neuropathic pain resulting from injury to motor efferent fibres, such as that in the ventral root transection (VRT) model. Capsaicin stimulation of afferent fibres was also shown to result in the release of BDNF into the spinal cord. Here, the effects of ablation of capsaicin-sensitive primary afferents (CSPAs) by local application of capsaicin on the sciatic nerve on VRT-induced mechanical hyperalgesia were observed.
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