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Application Area

Boc-Arg(Tos)-OH

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

Category

BOC-Amino Acids

Catalog number

BAT-002701

CAS number

13836-37-8

Molecular Formula

C18H28N4O6S

Molecular Weight

428.50

IUPAC Name

(2S)-5-[[amino-[(4-methylphenyl)sulfonylamino]methylidene]amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]pentanoic acid

Synonyms

Boc-Nω-4-toluenesulfonyl-L-arginine

Appearance

White powder

Purity

≥ 99.5% (HPLC, Chiral purity)

Density

1.31±0.1 g/cm3(Predicted)

Melting Point

~90 °C (dec.)

Storage

Store at 2-8°C

InChI

InChI=1S/C18H28N4O6S/c1-12-7-9-13(10-8-12)29(26,27)22-16(19)20-11-5-6-14(15(23)24)21-17(25)28-18(2,3)4/h7-10,14H,5-6,11H2,1-4H3,(H,21,25)(H,23,24)(H3,19,20,22)/t14-/m0/s1

InChI Key

WBIIPXYJAMICNU-AWEZNQCLSA-N

Canonical SMILES

CC1=CC=C(C=C1)S(=O)(=O)NC(=NCCCC(C(=O)O)NC(=O)OC(C)(C)C)N

Boc-Arg(Tos)-OH is a protected amino acid derivative used in peptide synthesis and biochemical research. Here are some key applications of Boc-Arg(Tos)-OH:

Peptide Synthesis: Boc-Arg(Tos)-OH is extensively used in the synthesis of peptides, where it serves as a protected arginine residue. Its Boc (tert-butoxycarbonyl) and Tos (tosyl) groups protect the amine and guanidine functionalities from unwanted reactions during peptide chain assembly. This allows for the precise construction of complex peptides with multiple arginine residues.

Drug Development: In the pharmaceutical industry, Boc-Arg(Tos)-OH is used to synthesize peptide-based drugs and investigational compounds. It plays a key role in the development of therapeutic peptides that target specific proteins or pathways involved in diseases. These peptides can be optimized for potency, stability, and bioavailability.

Structural Biology: Researchers use Boc-Arg(Tos)-OH in the study of protein structure and function. By incorporating this protected amino acid into synthetic peptides, scientists can probe protein interactions, binding sites, and conformational changes. This helps in elucidating the molecular mechanisms underpinning biological processes and disease states.

Bioconjugation: Boc-Arg(Tos)-OH is utilized in bioconjugation techniques to attach peptides to other molecules or surfaces. Its protected functional groups enable selective modification, making it useful for creating peptide-based probes, sensors, and biomaterials. These conjugates are valuable in diagnostics, therapeutics, and material science research.

1. New tris-alkoxycarbonyl arginine derivatives for peptide synthesis

Jan Izdebski, Tomasz Gers, Danuta Kunce, Pawe? Markowski J Pept Sci. 2005 Jan;11(1):60-4. doi: 10.1002/psc.585.

alpha-Alkoxycarbonyl protected ornithines were treated with N,N'-[Z(2Cl)](2)-S-methylisothiourea and N,N'-[Z(2Br)](2)-S-methylisothiourea, N,N'-Z(2)-S-methylisothiourea and N,N'-Boc(2)-S-methylisothiourea to form N(alpha, omega, omega')-tris-alkoxycarbonyl arginines. Two of them, Boc-Arg-{omega,omega'-[Z(2Br)](2)}-OH and Boc-Arg-{omega,omega'-[Z(2Cl)](2)}-OH, were used for the synthesis of dermorphin fragments containing two or three arginine residues. Examination of the products by HPLC and ESI-MS revealed that the purity of the materials obtained with the use of the new derivatives was higher than that obtained in concurrent syntheses in which Boc-Arg(Tos) was used.

2. Synthesis of arginine aldehydes for the preparation of pseudopeptides

G Guichard, J P Briand, M Friede Pept Res. 1993 May-Jun;6(3):121-4.

The synthesis of optically active aldehydes from N alpha-Boc-amino acids by reduction of the corresponding O,N-dimethyl-hydroxamates, while proceeding smoothly for most amino acids, has presented significant problems in the case of arginine. We demonstrate here that this difficulty can be overcome by the use of arginine derivatives in which the guanidino group is completely protected, such as in the case of N alpha-Boc-Arg(di-Z). In the case of nitro-, tosyl- or pmc-protected arginine, no satisfactory aldehyde formation can be obtained. It appears that in these cases the guanidino group is insufficiently protected and inhibits the formation of aldehydes. We also demonstrate that aldehydes can be readily obtained from N alpha-Fmoc protected amino acids.

3. Synthesis of N alpha-protected aminoacyl 7-amino-4-methyl-coumarin amide by phosphorous oxychloride and preparation of specific fluorogenic substrates for papain

L C Alves, P C Almeida, L Franzoni, L Juliano, M A Juliano Pept Res. 1996 Mar-Apr;9(2):92-6.

We report an improved procedure for the synthesis of fully protected aminoacyl 7-amino-4-methylcoumarin amide (MCA) employing the phosphorous oxychloride anhydride method. Seven Boc-X-MCA [where X = Arg(NG Tos), Cys(S-Bzl), Thr(O-Bzl), Ser(O-Bzl), Phe, Leu and Gly] and Z-Tyr(O-Me) were synthesized using this procedure, with yields ranging from 50% to 75%. These aminoacyl-MCA derivatives were employed for the synthesis of epsilon-NH2-caproyl-Leu-X-MCA, a fluorescent peptide series, which were assayed as papain substrates. All of them were completely hydrolyzed by papain, indicating that all of the Boc-X-MCA derivatives obtained were practically free of racemization. Since epsilon-NH2-Caproyl-Leu-(S-Bzl)Cys-MCA is very susceptible to hydrolysis by papain, quite resistant to hydrolysis by chymotrypsin and not hydrolyzed by trypsin, it is recommended for assays of thiol-proteinases in which specificity is required.