N-α-(t-Butoxycarbonyl)-L-arginine hydrochloride hydrate
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N-α-(t-Butoxycarbonyl)-L-arginine hydrochloride hydrate

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Category
BOC-Amino Acids
Catalog number
BAT-003115
CAS number
114622-81-0
Molecular Formula
C11H25ClN4O5
Molecular Weight
328.80
N-α-(t-Butoxycarbonyl)-L-arginine hydrochloride hydrate
IUPAC Name
(2S)-5-(diaminomethylideneamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid;hydrate;hydrochloride
Synonyms
Boc-Arg-OH HCl H2O; BOC-D-ARG(TOS)-OH ETOAC; D-Leucine; Nα-Boc-D-arginine Hydrochloride Monohydrate; Nα-(tert-Butoxycarbonyl)-D-arginine Hydrochloride Monohydrate; BOC-L-ARGININE HCl H2O; Boc-D-Arg-OH HCl H2O
Appearance
White powder
Purity
>98.0%(N)
Density
1.280 g/cm3
Melting Point
118.3 °C
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H22N4O4.ClH.H2O/c1-11(2,3)19-10(18)15-7(8(16)17)5-4-6-14-9(12)13;;/h7H,4-6H2,1-3H3,(H,15,18)(H,16,17)(H4,12,13,14);1H;1H2/t7-;;/m0../s1
InChI Key
OVXLPYFDJUFEHQ-KLXURFKVSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCCN=C(N)N)C(=O)O.O.Cl

N-α-(t-Butoxycarbonyl)-L-arginine hydrochloride hydrate, a specialized reagent with diverse applications in peptide synthesis and various analytical areas of bioscience, is a crucial component in cutting-edge research. Here are the key applications intricately presented with a high degree of perplexity and burstiness:

Peptide Synthesis: At the core of solid-phase peptide synthesis lies the role of N-α-(t-Butoxycarbonyl)-L-arginine hydrochloride hydrate, acting as a shielded amino acid that safeguards the arginine amino group with the t-Butoxycarbonyl (Boc) group during the elongation of molecular chains. This protective mechanism prevents undesired side reactions, ensuring the faithful construction of peptide sequences. Upon synthesis completion, the strategic removal of the Boc group results in the precise generation of the intended peptide, maintaining exact sequence accuracy amidst the molecular intricacies.

Protein Engineering: Venturing into the realm of protein engineering and the development of peptide-based therapeutics, this compound assumes a pivotal role in shaping innovations. By incorporating N-α-(t-Butoxycarbonyl)-L-arginine hydrochloride hydrate into peptide chains, researchers embark on an exploration of the profound impact arginine residues have on protein structure and function. This exploration plays a crucial part in the creation of novel proteins endowed with heightened therapeutic efficacy or structural stability, propelling transformative advancements within the expansive landscape of therapeutics and bioengineering.

Analytical Chemistry: Extending beyond the realms of synthesis, N-α-(t-Butoxycarbonyl)-L-arginine hydrochloride hydrate finds solid footing in the domain of analytical chemistry, particularly in the precise identification and quantification of arginine-containing peptides and proteins. Its inclusion in peptide standards plays a pivotal role in facilitating the accurate calibration of mass spectrometry and chromatography platforms, ensuring the utmost reliability and reproducibility of measurements in intricate proteomics investigations, where each detail holds significance in unraveling complex biological mysteries.

Bioconjugation: Embarking on the innovative path of bioconjugation, N-α-(t-Butoxycarbonyl)-L-arginine hydrochloride hydrate emerges as an invaluable tool for strategically introducing arginine residues into biomolecules, such as antibodies and nanoparticles. In its Boc-protected format, this compound enables selective functionalization without the cumbersome specter of cross-reactions, seamlessly ushering in the creation of precise targeted systems for drug delivery and diagnostic applications. This heralds a new era in precision medicine and diagnostics, where the convergence of biology and chemistry unlocks novel possibilities for advancing healthcare solutions.

1.Attenuation of the pressor response to exogenous angiotensin by angiotensin receptor blockers and benazepril hydrochloride in clinically normal cats.
Jenkins TL, Coleman AE, Schmiedt CW, Brown SA. Am J Vet Res. 2015 Sep;76(9):807-13. doi: 10.2460/ajvr.76.9.807.
OBJECTIVE: To compare the attenuation of the angiotensin I-induced blood pressure response by once-daily oral administration of various doses of angiotensin receptor blockers (irbesartan, telmisartan, and losartan), benazepril hydrochloride, or lactose monohydrate (placebo) for 8 days in clinically normal cats.
2.Salt forms of the pharmaceutical amide dihydrocarbamazepine.
Buist AR1, Kennedy AR1. Acta Crystallogr C Struct Chem. 2016 Feb 1;72(Pt 2):155-60. doi: 10.1107/S2053229616001133. Epub 2016 Jan 27.
Carbamazepine (CBZ) is well known as a model active pharmaceutical ingredient used in the study of polymorphism and the generation and comparison of cocrystal forms. The pharmaceutical amide dihydrocarbamazepine (DCBZ) is a less well known material and is largely of interest here as a structural congener of CBZ. Reaction of DCBZ with strong acids results in protonation of the amide functionality at the O atom and gives the salt forms dihydrocarbamazepine hydrochloride {systematic name: [(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium chloride, C15H15N2O(+)·Cl(-)}, dihydrocarbamazepine hydrochloride monohydrate {systematic name: [(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium chloride monohydrate, C15H15N2O(+)·Cl(-)·H2O} and dihydrocarbamazepine hydrobromide monohydrate {systematic name: [(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)(hydroxy)methylidene]azanium bromide monohydrate, C15H15N2O(+)·Br(-)·H2O}.
3.In vivo comet assay of acrylonitrile, 9-aminoacridine hydrochloride monohydrate and ethanol in rats.
Nakagawa Y1, Toyoizumi T2, Sui H2, Ohta R2, Kumagai F2, Usumi K2, Saito Y2, Yamakage K2. Mutat Res Genet Toxicol Environ Mutagen. 2015 Jul;786-788:104-13. doi: 10.1016/j.mrgentox.2015.04.001. Epub 2015 Apr 8.
As part of the Japanese Center for the Validation of Alternative Methods (JaCVAM)-initiative international validation study of the in vivo rat alkaline comet assay, we examined the ability of acrylonitrile, 9-aminoacridine hydrochloride monohydrate (9-AA), and ethanol to induce DNA damage in the liver and glandular stomach of male rats. Acrylonitrile is a genotoxic carcinogen, 9-AA is a genotoxic non-carcinogen, and ethanol is a non-genotoxic carcinogen. Positive results were obtained in the liver cells of male rats treated with known genotoxic compounds, acrylonitrile and 9-AA.
4.New Solid Forms of the Antiviral Drug Arbidol: Crystal Structures, Thermodynamic Stability, and Solubility.
Surov AO1, Manin AN1, Churakov AV2, Perlovich GL1. Mol Pharm. 2015 Nov 2;12(11):4154-65. doi: 10.1021/acs.molpharmaceut.5b00629. Epub 2015 Oct 19.
Salts of the antiviral drug Arbidol (umifenovir) with pharmaceutically relevant benzoate and salicylate anions were obtained, and their crystal structures were described. For Arbidol salicylate, an unstable solvate with acetonitrile was also found and characterized. Analysis of the conformational preferences of the Arbidol molecule in the crystal structures showed that it adopts two types of conformations, namely "open" and "closed", both of which correspond to local conformational energy minima of the isolated molecule. Thermal stability of the Arbidol salicylate solvates with chloroform and acetonitrile was analyzed by means of differential scanning calorimetry and thermogravimetric analysis. The standard thermodynamic functions of the salt formation were determined. The Gibbs energy change of the process was found to be negative, indicating that the formation of the salts from individual components is a spontaneous process. The dissolution study of the Arbidol salts performed in aqueous buffer solutions with pH 1.
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