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Application Area

H-β-HoAsp(OBzl)-OH

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

Category

β−Amino Acids

Catalog number

BAT-000875

Molecular Formula

C17H23NO6

Molecular Weight

337.37

Synonyms

H-beta-HoAsp(OBzl)-OH

Storage

Store at 2-8 °C

H-β-HoAsp(OBzl)-OH, a modified amino acid with diverse applications in bioscience and biotechnology, plays a pivotal role in various domains.

Peptide Synthesis: Widely employed in peptide synthesis, H-β-HoAsp(OBzl)-OH facilitates the creation of peptides, especially those incorporating modified or unnatural amino acids. Its integration aids in exploring the intricate structure-activity relationships of peptides, enhancing their stability and bioactivity. Researchers utilize this tool to tailor peptides for specific biological functions or therapeutic applications, unlocking a realm of possibilities in peptide-based research.

Protein Engineering: In the realm of protein engineering, H-β-HoAsp(OBzl)-OH proves invaluable for introducing targeted modifications into protein sequences. This enables scientists to probe the impacts of these alterations on protein folding, stability, and function. Such investigations are critical in the design of proteins with enhanced properties for industrial or medical applications, driving advancements in the field of biotechnology and personalized medicine.

Drug Design and Development: Serving as a foundational component in the development of peptide-based therapeutics, H-β-HoAsp(OBzl)-OH plays a critical role in enhancing the pharmacokinetic properties and target specificity of designed peptides. By incorporating this modified amino acid, researchers can fashion peptides with superior therapeutic potential for combating diseases like cancer, diabetes, and infectious diseases.

Chemical Biology: A key player in chemical biology, H-β-HoAsp(OBzl)-OH serves as a powerful tool for investigating cellular processes and protein interactions at the molecular level. Its unique characteristics make it a versatile probe for delving into biological mechanisms, aiding in the unraveling of fundamental pathways and the development of cutting-edge biomedical research tools.

1. Rhodium(I)-Catalyzed

B Witulski, T Stengel Angew Chem Int Ed Engl. 1999 Aug;38(16):2426-2430.

The regiospecific introduction of substituents into the 4-position of 2,3-dihydroindoles (indolines), which is significant for the synthesis of various natural products and pharmaceuticals, was achieved by rhodium(I)-catalyzed cyclotrimerizations of 1 with acetylene to give 2. Up to four substituents can be introduced simultaneously into the indoline core by using this novel strategy. R=OH, OBzl, Otetrahydropyranyl, NHSO(2)C(6)H(4)CH(3); Ts=H(3)CC(6)H(4)SO(2).

2. Synthesis and crystal structures of Boc-L-Asn-L-Pro-OBzl.CH3OH and dehydration side product, Boc-beta-cyano-L-alanine-L-Pro-OBzl

A N Stroup, L B Cole, M M Dhingra, L M Gierasch Int J Pept Protein Res. 1990 Dec;36(6):531-7. doi: 10.1111/j.1399-3011.1990.tb00992.x.

Boc-L-Asn-L-Pro-OBzl: C21H29O6N3.CH3OH, Mr = 419.48 + CH3 OH, monoclinic, P2(1), a = 10.049(1), b = 10.399(2), c = 11.702(1) A, beta = 92.50(1)degrees, V = 1221.7(3) A3, dx = 1.14 g.cm-3, Z = 2, CuK alpha (lambda = 1.54178 A), F(000) = 484 (with solvent), 23 degrees, unique reflections (I greater than 3 sigma(I)) = 1745, R = 0.043, Rw = 0.062, S = 1.66. Boc-beta-cyano-L-alanine-L-Pro-OBzl: C21H27O5N3, Mr = 401.46, orthorhombic, P2(1)2(1)2(1), a = 15.741(3), b = 21.060(3), c = 6.496(3) A, V = 2153(1) A3, dx = 1.24 g.cm-3, Z = 4, CuK alpha (lambda = 1.54178 A), F(000) = 856, 23 degrees, unique reflections (I greater than 3 sigma(I)) = 1573, R = 0.055, Rw = 0.078, S = 1.86. The tert.-butyloxycarbonyl (Boc) protected dipeptide benzyl ester (OBzl), Boc-L-Asn-L-Pro-OBzl, prepared from a mixed anhydride reaction using isobutylchloroformate, Boc-L-asparagine, and HCl.L-proline-OBzl, crystallized with one methanol per asymmetric unit in an extended conformation with the Asn-Pro peptide bond trans. Intermolecular hydrogen bonding occurs between the methanol and the Asn side chain and between the peptide backbone and the Asn side chain. A minor impurity due to the dehydration of the Asn side chain to a beta-CNala crystallized with a similar extended conformation and a single intermolecular hydrogen bond.

3. Amino acids and peptides. XVIII. Dipeptide formation during the synthesis of Z-Asp(OBzl)-OH

S Iguchi, K Kawasaki, Y Okada Int J Pept Protein Res. 1987 Nov;30(5):695-700. doi: 10.1111/j.1399-3011.1987.tb03382.x.

During the benzyloxycarbonylation of H-Asp(OBzl)-OH by the Schotten-Bauman reaction with benzyloxycarbonyl chloride in the presence of NaHCO3 or Na2CO3, besides Z-Asp(OBzl)-OH, Z-Asp(OBzl)-Asp(OBzl)-OH was formed as side product, although the extent of the dipeptide formation differed depending on the base used (10% and 20% respectively). It was found that melting point, rotation value and Rf values upon thin-layer chromatography of Z-Asp(OBzl)-Asp(OBzl)-OH were quite similar to those of Z-Asp(OBzl)-OH.