H-Arg(NO2)-Obzl
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H-Arg(NO2)-Obzl

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Category
Other Unnatural Amino Acids
Catalog number
BAT-015672
CAS number
7672-27-7
Molecular Formula
C13H19N5O4
Molecular Weight
309.32
H-Arg(NO2)-Obzl
IUPAC Name
benzyl (2S)-2-amino-5-[[amino(nitramido)methylidene]amino]pentanoate
Synonyms
L-Nabe; N-Nitro-L-argininebenzyl ester; benzyl Nw-nitro-L-argininate; (S)-Benzyl 2-amino-5-(3-nitroguanidino)pentanoate
Density
1.37 g/cm3
Melting Point
132-134°C
InChI
InChI=1S/C13H19N5O4/c14-11(7-4-8-16-13(15)17-18(20)21)12(19)22-9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9,14H2,(H3,15,16,17)/t11-/m0/s1
InChI Key
FAJFGLZHUIUNSS-NSHDSACASA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)C(CCCN=C(N)N[N+](=O)[O-])N

H-Arg(NO2)-Obzl, also known as Nω-nitro-L-arginine benzyl ester, is a chemical compound often used in biochemical research. Here are some key applications of H-Arg(NO2)-Obzl:

Enzyme Inhibition Studies: H-Arg(NO2)-Obzl is commonly used as an inhibitor in enzyme studies to probe the function of nitric oxide synthase (NOS). By binding to the active sites of NOS, it helps researchers understand the enzyme’s role in various physiological processes. This information can be crucial for developing therapeutic strategies for conditions involving nitric oxide signaling.

Nitric Oxide Pathway Research: In cellular and molecular biology, H-Arg(NO2)-Obzl is employed to study nitric oxide (NO) synthesis and signaling pathways. By inhibiting NO production, researchers can observe the downstream effects and uncover the role of NO in cell signaling, vascular regulation, and immune response. This knowledge can pave the way for new insights into cardiovascular and neurodegenerative diseases.

Drug Development: H-Arg(NO2)-Obzl serves as a pharmacological tool in the development of drugs targeting the nitric oxide pathway. Its selective inhibition of NOS can help identify potential therapeutic targets and lead compounds for treating diseases associated with dysregulated nitric oxide levels, such as hypertension and inflammatory disorders. Researchers use it to validate the efficacy and specificity of new drug candidates.

Biomedical Research: In the field of biomedical research, H-Arg(NO2)-Obzl is utilized to explore the physiological and pathophysiological roles of nitric oxide. It helps in elucidating NO’s involvement in processes like blood flow regulation, neurotransmission, and immune defense. This compound provides a basis for better understanding how nitric oxide contributes to health and disease, guiding future research endeavors.

1. Synthesis of modified tuftsins containing monosaccharides or monosaccharide derivatives
R Rocchi, L Biondi, F Filira, M Gobbo, S Dagan, M Fridkin Int J Pept Protein Res. 1987 Feb;29(2):250-61. doi: 10.1111/j.1399-3011.1987.tb02252.x.
Synthesis of some modified tuftsins is described in which a monosaccharide or a monosaccharide derivative was incorporated in the molecule. Acylation of H-Thr-Lys(Z)-Pro-Arg(NO2)-OBzl with D(+)-gluco-1,5-lactone followed by catalytic hydrogenation gave N alpha-gluconyl-tuftsin. Glycosylation of the carboxyl function of the C-terminal arginine has been achieved by reacting, through the mixed anhydride procedure, Boc-Thr-Lys(Z)-Pro-OH with 2-deoxy-2-(NG-nitroargininamido)-D-glucopyranose followed by catalytic hydrogenation and trifluoroacetic acid treatment. O-Glucosyl-tuftsin has been prepared by reacting o-nitrophenyl N-benzyloxycarbonyl-O-[(alpha + beta) 2,3,4,6-tetra-O-benzyl-D-glucopyranosyl]-threoninate with H-Lys(Z)-Pro-Arg(NO2)-OBzl in the presence of 1-hydroxybenzotriazole. Flash chromatography on silica gel allowed a partial separation of the diastereoisomers, one of which has been isolated in a reasonable yield. The single diastereoisomer and the alpha + beta anomeric mixture were separately deblocked by catalytic hydrogenation and purified by RP-HPLC.
2. Synthesis of glycosylated tuftsins and tuftsin-containing IgG fragment undecapeptide
L Biondi, F Filira, M Gobbo, B Scolaro, R Rocchi Int J Pept Protein Res. 1991 Feb;37(2):112-21. doi: 10.1111/j.1399-3011.1991.tb00090.x.
Syntheses are described of two new tuftsin derivatives containing a 2-acetamido-2-deoxy-D-galactopyranosyl unit alpha- or beta-glycosidically linked to the threonine's hydroxy side chain function and of the glycosylated undecapeptide corresponding to the tuftsin region of the heavy chain of IgG (amino acid sequence 289-299). The glycosylated tuftsins were synthesized by the solution procedure. Fmoc-[Gal NAc(Ac)3 alpha]Thr-OH and Fmoc-[GalNAc(Ac)3 beta]Thr-OH were allowed to react with H-Lys(Z)-Pro-Arg(NO2)-OBzl by the mixed anhydride procedure and the resulting glycosylated tetrapeptides were fully deblocked by catalytic hydrogenation followed by treatment with potassium cyanide, purified by ion exchange chromatography and characterized by analytical HPLC, elemental and amino acid analyses, optical rotation, and proton NMR spectroscopy. Synthesis of the glycosylated undecapeptide was achieved by the continuous flow solid phase procedure on 4-hydroxymethylphenoxyacetyl-norleucyl derivatized Kieselguhr-supported resin. Fmoc-amino acid symmetrical anhydrides or pentafluorophenyl esters, in the presence of N-hydroxybenzotriazole, were used as the acylating agents. To mimic the native sequence of the tuftsin region at the Fc-domain of immunoglobulin G a 2-acetamido-2-deoxy-beta-D-glucopyranosyl unit was N-glycosidically linked to the amide side chain of Asn 297. The glycosylated asparagine residue was introduced as N2-fluorenylmethyloxycarbonyl-N4-(2-acetamido-3,4,6-tri-O-acetyl-2 -deoxy-beta-D - glucopyranosyl)-asparagine pentafluorophenyl ester. After cleavage from the resin the glycopeptide was deprotected, purified by ion exchange chromatography, and characterized by analytical HPLC, amino acid analysis, high voltage electrophoresis, and proton NMR. The conformational features of the glyco-undecapeptide were determined by circular dichroism measurements both in water and in 98% trifluoroethanol. Results of biological assays will be published elsewhere.
3. Synthesis of O-glycosylated tuftsins by utilizing threonine derivatives containing an unprotected monosaccharide moiety
F Filira, L Biondi, F Cavaggion, B Scolaro, R Rocchi Int J Pept Protein Res. 1990 Jul;36(1):86-96. doi: 10.1111/j.1399-3011.1990.tb00086.x.
Synthesis is described of four tuftsin derivatives containing a D-glucopyranosyl or a D-galactopyranosyl unit covalently linked to the hydroxy side chain function of the threonine residue through either an alpha or beta O-glycosidic linkage. Fmoc-threonine derivatives containing the suitable unprotected sugar were used for incorporating the O-glycosylated amino acid residue. Z-Thr[alpha-Glc(OBzl)4]-OBzl and Z-Thr[alpha-Gal(OBzl)4]-OBzl were prepared from the tetra-O-benzylated sugar and Z-Thr-OBzl by the trichloroacetimidate method in the presence of trimethylsilyl trifluoromethane sulfonate. The alpha glycosylated threonine derivatives were converted into Fmoc-Thr(alpha-Glc)-OH and Fmoc-Thr(alpha-Gal)-OH by catalytic hydrogenation followed by acylation with Fmoc-OSu. beta-Glucosylation and beta-galactosylation of threonine were carried out by reacting the proper per-O-acetylated sugar with Z-Thr-OBzl and boron trifluoride ethyl etherate in dichloromethane. Catalytic hydrogenation of the beta-O-glycosylated threonine derivatives followed by acylation with Fmoc-OSu and deacetylation with methanolic hydrazine yielded Fmoc-Thr(beta-Glc)-OH and Fmoc-Thr(beta-Gal)-OH, respectively. The O-glycosylated threonine derivatives were then reacted with H-Lys(Z)-Pro-Arg(NO2)-OBzl in the presence of DCC and HOBt and the resulting glycosylated tuftsin derivatives were fully deblocked by catalytic hydrogenation, purified by HPLC, and characterized by optical rotation, amino acid analysis, and 1H NMR. The beta-galactosylated tuftsin was also prepared by the continuous flow solid phase procedure.
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