Boc-Arg-OH
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Boc-Arg-OH

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Category
BOC-Amino Acids
Catalog number
BAT-000783
CAS number
13726-76-6
Molecular Formula
C11H22N4O4
Molecular Weight
274.32
Boc-Arg-OH
IUPAC Name
(2S)-5-(diaminomethylideneamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid
Synonyms
(S)-2-((tert-Butoxycarbonyl)amino)-5-guanidinopentanoic acid; Boc-L-Arg-OH
Related CAS
35897-34-8 (hydrochloride)
Storage
Store at 2-8 °C
InChI
InChI=1S/C11H22N4O4/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)/t7-/m0/s1
InChI Key
HSQIYOPBCOPMSS-ZETCQYMHSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCCN=C(N)N)C(=O)O

Boc-Arg-OH, also known as N-Boc-arginine, is a chemical compound widely employed in peptide synthesis and diverse biochemical applications. Here are the key applications of this compound, presented with high perplexity and burstiness:

Peptide Synthesis: Serving as a fundamental building block in peptide and protein synthesis, Boc-Arg-OH plays a pivotal role in the precise assembly of peptides for various research and therapeutic purposes. Shielded by the Boc (tert-butyloxycarbonyl) group, the arginine residue seamlessly integrates into peptide sequences, avoiding undesirable reactions. This methodical approach enables the meticulous construction of peptides, advancing scientific exploration and drug development endeavors.

Pharmaceutical Development: Within the realm of pharmaceutical innovation, Boc-Arg-OH is a cornerstone in the development of peptide-based drugs with enhanced stability and functionality. Enabling the creation of potent therapeutic agents targeting a spectrum of diseases, including cancer and infectious ailments, this compound contributes to the synthesis of pure and efficient drugs through solid-phase peptide synthesis (SPPS). Its strategic utilization propels the advancement of drug discovery and delivery mechanisms.

Biochemical Research: In the realm of biochemical inquiry, Boc-Arg-OH serves as a valuable tool for investigating protein-protein interactions and enzyme kinetics. By incorporating arginine residues safeguarded by the Boc group into peptides, researchers can illuminate the intricate roles of these amino acids in diverse biological processes. This analytical approach aids in deciphering the molecular mechanisms underpinning cellular events, enriching our understanding of the intricate biochemical pathways guiding life's processes.

Protein Engineering: Within the domain of protein engineering, Boc-Arg-OH emerges as a key player in tailored modifications to enhance the functional properties of proteins. Through the selective introduction of this Boc-protected arginine at specific sites within a protein, researchers delve into the impacts on protein folding, stability, and activity. This acquired knowledge lays the foundation for designing novel proteins with heightened functionalities, catering to industrial and therapeutic applications, thereby expanding the frontier of protein engineering possibilities.

1. Side-Chain Protonation States of a Fluorescent Arginine
Sarah R Marshall, Mikayla L Stoudt, Madeleine A DiVittorio, Andrew L Sargent, William E Allen J Org Chem. 2019 Nov 15;84(22):14407-14413. doi: 10.1021/acs.joc.9b00677. Epub 2019 Oct 25.
An arginine derivative with a fluorescent side-chain, Boc-Arg(Nap)-OH, was prepared by palladium(0)-catalyzed coupling of Boc-Arg-OH with a 4-bromonaphthalimide. The presence of the fluorophore lowers the pKa of the side-chain guanidinium group by several orders of magnitude, to 9.0 (±0.1), allowing the derivative to access an electrically neutral protonation state that is not generally available to arginine itself. Computational modeling (DFT) predicts that protonation takes place at the side-chain C═N atom that bears the fluorophore. Calculated electronic absorptions for the protonated (356 nm) and neutral species (440 nm) are in good agreement with experiment. When irradiated with light, excited-state proton transfer (ESPT) occurs from cationic side-chains to suitably basic solvents, resulting in fluorescence emission from the neutral species. Arg(Nap) can be incorporated into peptides with sterically accessible N-termini using specially adapted conditions of solid-phase peptide synthesis.
2. Comparison of Color Development Kinetics of Tanning Reactions of Dihydroxyacetone with Free and Protected Basic Amino Acids
Yufa Sun, Subin Lee, Long Lin ACS Omega. 2022 Dec 1;7(49):45510-45517. doi: 10.1021/acsomega.2c06124. eCollection 2022 Dec 13.
Sunless tanning has become incredibly prevalent due to the increasing fashionable demand and the awareness of photodamage risks. The brown pigments are induced by dihydroxyacetone (DHA) and amino groups in the stratum corneum (SC) of skin via the Maillard reaction. While most studies concerning sunless tanning reactions have focused on free amino acids (AAs), little information is available on the impact of the side chain of AAs or proteins on this important reaction in cosmetic chemistry. To explore the reactivity and color development kinetics of different types of amino groups, three basic free AAs (Arg, His, and Lys) and three Nα-protected AAs (Boc-Arg-OH, Boc-His-OH, and Boc-Lys-OH) were used to react with DHA using a simplified model system at different reaction times, pH, and temperatures. Full factorial experiments were employed to design and analyze the effects of these three factors. The browning intensity and color characteristics were quantitatively evaluated. The factorial experiments showed that temperature had the most significant influence on the browning intensity and played a dominant role in the interactions with the reaction time and pH. It was found, for the first time, that Arg and His reacted with DHA more rapidly than Boc-Arg-OH and Boc-His-OH, while Boc-Lys-OH developed a stronger color than Lys under the same conditions, suggesting that ε-NH2 of a lysine residue in peptides or proteins of SC may play a crucial role in the color development of DHA tanning. This study not only clearly illustrates the capability of the side chain of AAs to produce colored compounds but also provides a deeper understanding of DHA tanning.
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