Nα-Fmoc-Nù,ù-dimethyl-L-arginine (symmetrical) hydrochloride
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Nα-Fmoc-Nù,ù-dimethyl-L-arginine (symmetrical) hydrochloride

* Please kindly note that our products are not to be used for therapeutic purposes and cannot be sold to patients.

Category
Fmoc-Amino Acids
Catalog number
BAT-000458
CAS number
1330286-46-8
Molecular Formula
C23H28N4O4·HCl
Molecular Weight
461.00
IUPAC Name
(2S)-5-[(N,N'-dimethylcarbamimidoyl)amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)pentanoic acid;hydrochloride
Synonyms
Fmoc-L-Arg(Me)2-OH HCl (symmetrical)
Appearance
White to off-white powder
Purity
≥ 95% (HPLC)
Storage
Store at 2-8 °C
InChI
InChI=1S/C23H28N4O4.ClH/c1-24-22(25-2)26-13-7-12-20(21(28)29)27-23(30)31-14-19-17-10-5-3-8-15(17)16-9-4-6-11-18(16)19;/h3-6,8-11,19-20H,7,12-14H2,1-2H3,(H,27,30)(H,28,29)(H2,24,25,26);1H/t20-;/m0./s1
InChI Key
YICQYUMPVBAXNV-BDQAORGHSA-N
Canonical SMILES
CNC(=NC)NCCCC(C(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13.Cl

Nα-Fmoc-Nù,ù-dimethyl-L-arginine (symmetrical) hydrochloride is a specialized chemical reagent utilized in peptide synthesis and molecular biology. Here are the key applications of Nα-Fmoc-Nωω-dimethyl-L-arginine (symmetrical) hydrochloride:

Peptide Synthesis: At the forefront of solid-phase peptide synthesis, Nα-Fmoc-Nù,ù-dimethyl-L-arginine plays a pivotal role in introducing arginine residues with precise methyl modifications. These modifications are instrumental in investigating the significance of methylated arginine in protein-protein interactions and post-translational modifications. The reagent’s Fmoc group serves as a protective shield, facilitating the seamless elongation of peptides with unparalleled efficiency and precision.

Protein Function Studies: In the realm of protein function research, this compound is a cornerstone in synthesizing peptides that mimic methylated arginine residues present in diverse proteins. By incorporating Nα-Fmoc-Nù,ù-dimethyl-L-arginine into peptides, researchers embark on a journey to explore how arginine methylation influences protein binding activity and stability. This application holds immense importance in unraveling the intricate regulatory mechanisms governing cellular processes, shedding light on the molecular choreography within cells.

Epigenetics Research: Delving into the realm of epigenetics, arginine methylation emerges as a crucial epigenetic mark with this reagent serving as a catalyst in generating peptides and proteins bearing specific methylation patterns. Through the craft of such biomolecules, scientists embark on a quest to decipher the impact of arginine methylation on gene expression and chromatin modifications. These profound insights are pivotal in unraveling the tapestry of epigenetic regulation, paving the way for the development of novel therapeutic strategies targeting epigenetic pathways and reshaping our understanding of gene regulation.

Development of Methylarginine-Specific Antibodies: A cornerstone in the production of methylated peptides acting as antigens, this reagent fuels the creation of antibodies tailored to dimethyl-arginine residues. These antibodies stand as sentinels, actively engaged in the detection and quantification of methylated arginine within biological samples. This application plays a foundational role in advancing research endeavors aimed at identifying and characterizing protein methylation patterns in diverse diseases and physiological conditions, spotlighting the role of methylated arginine in shaping biological outcomes.

1. 3-Methyl-1,2,3,4,5,6,1',2',3',4'-deca-hydro-spiro-[benz[f]isoquinoline-1,2'-naphthalen]-1'-one
Sohro Siaka, Anatoly T Soldatenkov, Anastasia V Malkova, Elena A Sorokina, Victor N Khrustalev Acta Crystallogr Sect E Struct Rep Online. 2012 Nov 1;68(Pt 11):o3230. doi: 10.1107/S1600536812043309. Epub 2012 Oct 27.
The title compound, C(23)H(23)NO, is the product of a tandem transformation of the double Mannich base bis-(1-oxo-1,2,3,4-tertrahydro-2-naphtho-ylmeth-yl)amine hydro-chloride in HBr solution upon heating. The tetra-hydro-pyridine ring has a non-symmetrical half-chair conformation, whereas the cyclo-hexa-diene and cyclo-hexene rings adopt non-symmetrical half-boat conformations. The dihedral angle between the planes of the terminal benzene rings is 62.85 (6)°. The N atom has a trigonal-pyramidal geometry [sum of the bond angles = 332.4 (3)°]. In the crystal, mol-ecules form [001] chains via weak non-classical C-H⋯N hydrogen bonds. The chains are stacked along the b axis.
2. Bullous Prurigo Pigmentosa
Xinjun Wang, Chenchen Xu Open Life Sci. 2019 Jul 10;14:214-216. doi: 10.1515/biol-2019-0024. eCollection 2019 Jan.
Prurigo pigmentosa (PP) is an inflammatory dermatosis with unknown etiology. The clinical presentations of PP varies according to the stages of the disease. Rarely, the formation of numerous vesicles and bullae upon erythematous infiltrative plaques can be found during the entire clinical course. In the present case, a 29-year-old Chinese woman presented with a 6-year history of relapsing pruritic erythematous plaques and bulla on her neck, chest and back. Physical examination revealed multiple erythematous plaques and vesicles in combination with mottled pigmentation in a symmetrical distribution and reticular pattern on the nape of her neck, chest and back. Histological examination of the biopsy specimen collected from the bullous area of her chest indicated a lichenoid reaction with intraepidermal bulla. This inflammatory region is characterized by recruitment of lymphocytes, spongiosis, and a perivascular lymphohistiocytic infiltrate in the upper dermis. Direct immunofluorescence analysis for IgG, IgA, IgM and C3 was negative. The diagnosis of bullous prurigo pigmentosa was verified based on the clinical manifestation and pathological findings. Minocycline hydrochloride therapy (100mg/d) was initiated, and 3 weeks later the rash had completely disappeared, which resulted in pigmentation of the entire area. No recurrence was observed during the 4 years follow-up.
3. Management of diabetic neuropathy
Simona Cernea, Itamar Raz Metabolism. 2021 Oct;123:154867. doi: 10.1016/j.metabol.2021.154867. Epub 2021 Aug 17.
Diabetic neuropathy is a neurodegenerative disorder that may alter both the somatic and autonomic peripheral nervous systems in the context of diabetes mellitus (DM). It is a prevalent and burdensome chronic complication of DM, that requires timely management. Optimized glycemic control (mainly for type 1 DM), multifactorial intervention (mainly for type 2 DM), with lifestyle intervention/physical exercise, and weight loss represent the basis of management for diabetic distal symmetrical polyneuropathy, and should be implemented early in the disease course. Despite better understanding of the pathogenetic mechanisms of diabetic peripheral neuropathy, there is still a stringent need for more pathogenetic-based agents that would significantly modify the natural history of the disease. The paper reviews the available drugs and current recommendations for the management of distal symmetrical polyneuropathy, including pain management, and for diabetic autonomic neuropathy. Evaluation of drug combinations that would perhaps be more efficient in slowing the progression of the disease or even reversing it, and that would provide a better pain management is still needed.
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