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Nα-Boc-L-asparagine

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

Nα-Boc-L-asparagine is an N-Boc-protected form of L-Asparagine. L-Asparagine was first isolated by Robiquet and Vauquelin from asparagus juice (a high source of L-asparagine). L-Asparagine is often incorporated into proteins, and is a basis for some cancer therapies as certain cancerous cells require L-asparagine for growth.

Category

BOC-Amino Acids

Catalog number

BAT-002924

CAS number

7536-55-2

Molecular Formula

C9H16N2O5

Molecular Weight

232.20

IUPAC Name

(2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid

Synonyms

Boc-L-Asn-OH; Boc-(S)-2-aminosuccinic acid 4-amide monohydrate; (2S)-4-amino-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoic acid; N-BOC-L-asparagine; Boc-Asn; Nalpha-(tert-Butoxycarbonyl)-L-asparagine

Appearance

White powder

Purity

≥ 99.9% (Chiral HPLC)

Density

1.253 g/cm3

Melting Point

170-175 °C

Boiling Point

481.7 °C at 760 mmHg

Storage

Store at 2-8 °C

InChI

InChI=1S/C9H16N2O5/c1-9(2,3)16-8(15)11-5(7(13)14)4-6(10)12/h5H,4H2,1-3H3,(H2,10,12)(H,11,15)(H,13,14)/t5-/m0/s1

InChI Key

FYYSQDHBALBGHX-YFKPBYRVSA-N

Canonical SMILES

CC(C)(C)OC(=O)NC(CC(=O)N)C(=O)O

Nα-Boc-L-asparagine, a crucial protected amino acid derivative, holds immense significance in peptide synthesis and pharmaceutical research. Delve into the key applications of Nα-Boc-L-asparagine presented with high perplexity and burstiness.

Peptide Synthesis: Serving as a foundational component in solid-phase peptide synthesis, Nα-Boc-L-asparagine stands as a pivotal element in building peptides and proteins. With its Boc protective group ensuring precise amino acid integration, undesired side reactions are effectively thwarted. This method enables the creation of exceptionally pure peptides tailored for diverse research and therapeutic endeavors.

Drug Development: In the dynamic realm of pharmaceutical exploration, Nα-Boc-L-asparagine emerges as a critical linchpin in synthesizing drug candidates and bioactive peptides. Researchers leverage this compound to delve into intricate structure-activity relationships, ultimately honing lead compounds for heightened efficacy and selectivity. The evaluation of various analogs of asparagine-containing peptides opens avenues for potent therapeutic development.

Structural Biology: Extending its utility into the domain of structural biology, Nα-Boc-L-asparagine facilitates the production of peptides essential for studies involving NMR and X-ray crystallography. These cutting-edge techniques mandate high-quality peptide samples to unveil the three-dimensional architectures of proteins and protein-ligand complexes. Insights gleaned from structural analyses play a pivotal role in unraveling protein functionalities and in designing novel pharmaceutical agents.

Bioconjugation: Positioned as a key player in bioconjugation techniques, Nα-Boc-L-asparagine enables the modification of peptides and proteins with diverse functional groups. This versatility allows for attaching tags, labels, or other molecules to explore protein interactions, localization, and functions. Such modifications are indispensable for a plethora of biochemical assays and therapeutic applications, including the development of targeted drug delivery systems.

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

Stroup AN1, Cole LB, Dhingra MM, Gierasch LM. Int J Pept Protein Res. 1990 Dec;36(6):531-7.

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.

2.The Enantiospecific Synthesis of an Isoxazoline. A RGD Mimic Platelet GPIIb/IIIa Antagonist.

Zhang Lh1, Chung JC, Costello TD, Valvis I, Ma P, Kauffman S, Ward R. J Org Chem. 1997 Apr 18;62(8):2466-2470.

A convergent, large-scale, chiral synthesis of isoxazoline 1 has been achieved in 37% overall yield and >99.6% optical purity, starting from L-asparagine and 4-cyanobenzaldehyde. Hofmann reaction of N(alpha)-n-Boc-L-asparagine with iodosobenzene diacetate provides optically pure N(alpha)-n-Boc-L-alpha,beta-diaminopropionic acid (8) in 75% yield. A process of lipase resolution-base catalyzed epimerization gives the single enantiomer 5. Reaction of acid 5 with amine 9 in the presence of thionyl chloride forms the framework of 1. A Pinner reaction of intermediate 4 in methyl acetate or anisole, followed by an amidination with ammonium acetate, gives optically pure product 1.

3.Appraisal of a glycopeptide cloaking strategy for a therapeutic oligopeptide: glycopeptide analogs of the renin inhibitor ditekiren.

Harrison AW1, Fisher JF, Guido DM, Couch SJ, Lawson JA, Sutter DM, Williams MV, DeGraaf GL, Rogers JE, Pals DT, et al. Bioorg Med Chem. 1994 Dec;2(12):1339-61.

Among the limitations to the practical therapeutic oligopeptide are low oral availability, indifferent aqueous solubility, and an astonishing efficient sequestration and biliary elimination by a multi-capacity liver transporter. Given the purposed use of N- and O- linked saccharides as functional appendages of eukaryotic peptides and proteins, a strategy of glycopeptide mimicry was examined for the oligopeptide renin inhibitor, ditekiren. The anticipation was that the saccharide would impart significant aqueous solubility, and might impact beneficially on the remaining two limitations. Execution of this approach was achieved by the removal of the (dimethylethoxy)carbonyl amino terminus of ditekiren, and its substitution by Boc-L-asparagine N-linked mono- and disaccharides. Potent hypotensive activity, as measured by a human renin-infused rat assay, is observed for virtually all of these structures (N-linked beta-pyranose D-N-acetyglucosaminyl, D-glucosaminyl, D-N-acetylgalactosaminyl, D-mannosyl, D-galactosyl, D-maltosyl, D-cellobiosyl, D-chitobiosyl, but not L-fucosyl).