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Application Area

Boc-L-asparaginol

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

Category

Amino Alcohol

Catalog number

BAT-002624

CAS number

30044-67-8

Molecular Formula

C9H18N2O4

Molecular Weight

218.20

IUPAC Name

tert-butyl N-[(2S)-4-amino-1-hydroxy-4-oxobutan-2-yl]carbamate

Synonyms

Nα-Boc-L-Asn-ol; N-Boc-L-asparaginol; (S)-tert-Butyl (4-amino-1-hydroxy-4-oxobutan-2-yl)carbamate

Appearance

White to off-white powder

Purity

≥ 98% (HPLC)

Density

1.16 g/cm3

Melting Point

112-123 °C

Boiling Point

456.4°C

Storage

Store at 2-8 °C

InChI

InChI=1S/C9H18N2O4/c1-9(2,3)15-8(14)11-6(5-12)4-7(10)13/h6,12H,4-5H2,1-3H3,(H2,10,13)(H,11,14)/t6-/m0/s1

InChI Key

BYCKHNZSBNGBQL-LURJTMIESA-N

Canonical SMILES

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

Boc-L-asparaginol, a pivotal intermediate in peptide synthesis, finds diverse applications in bioscientific research and industry. Here, we explore four key applications of Boc-L-asparaginol with a high degree of perplexity and burstiness.

Peptide Synthesis: Widely utilized as a foundational unit in peptide synthesis, Boc-L-asparaginol plays a crucial role. The Boc (tert-butoxycarbonyl) group serves as a shield for the amine functionality, enabling targeted reactions at specific sites. This essential feature makes it a fundamental building block for the creation of a wide array of peptides, serving both research and therapeutic objectives.

Drug Development: In the realm of pharmaceutical investigation, Boc-L-asparaginol emerges as a vital tool for synthesizing potential drug candidates and exploring their biological functions. Its contribution to the production of intricate molecules aids researchers in deciphering drug-receptor interactions and refining drug design strategies. This advancement holds the promise of uncovering novel therapeutic solutions for a multitude of ailments.

Bioconjugation: The versatile nature of Boc-L-asparaginol extends to the realm of bioconjugation, where it facilitates the attachment of peptides and small molecules to larger biomolecules like proteins and antibodies. This process is critical for the development of precise targeted drug delivery systems and diagnostic apparatus. The temporary protection provided by the Boc group during synthesis allows for controlled attachment, which can be selectively removed under gentle conditions to expose the reactive amine.

Protein Engineering: In the domain of protein manipulation, Boc-L-asparaginol comes into play as a key component for inducing specific alterations and exploring the intricate relationship between protein structure and function. By integrating this amino acid derivative into proteins, scientists can craft customized variants with desired characteristics. This strategic approach aids in unraveling the dynamics of proteins and formulating proteins with elevated stability and activity levels, catering to both industrial and therapeutic demands.

1.Aza-peptides. III. Experimental structural analysis of aza-alanine and aza-asparagine-containing peptides.

André F1, Vicherat A, Boussard G, Aubry A, Marraud M. J Pept Res. 1997 Nov;50(5):372-81.

To determine the structural perturbations induced by the C alpha H-->N alpha exchange in aza-peptides, we have examined by 1H NMR and IR spectroscopy various derivatives of the aza-analogues of alanine, aspartic acid and asparagine in different organic solvents with increasing polarity. Their general formulas are: R1-AzXaa-NR2R3, R1-Pro-AzXaa-NR2R3 and R1-AzXaa-Pro-NR2R3 (where AzXaa denotes the aza-analogue of the amino acid residue Xaa = Ala, Asp, Asn; R1 = Boc, Z; R2, R3 = H, Me, iPr). The aza-analogue of an amino acid residue appears to be a strong beta-turn-inducing motif, and the AzAsn carboxamide side-chain is capable of interacting, as a proton donor, with the preceding peptide carbonyl group.

2.Homochiral 4-azalysine building blocks: syntheses and applications in solid-phase chemistry.

Chhabra SR1, Mahajan A, Chan WC. J Org Chem. 2002 Jun 14;67(12):4017-29.

Anomalous amino acids not only play central roles as mimics of natural amino acids but also offer opportunities as unique building blocks for combinatorial chemistry. This paper describes the chiral syntheses and solid-phase applications of a versatile atypical amino acid, 4-azalysine (2,6-diamino-4-azahexanoic acid) 1. The syntheses of differentially protected 4-azalysine derivatives 28a-e have been developed by two efficient and inexpensive routes that start either from Garner's aldehyde 16 or the chiron (S)-N(alpha)-Cbz-2,3-diaminopropionic acid 23. Both approaches employ the convergent modular concept and exploit reductive amination of aldehydes with amines as the key step for the fusion of the two segments. In the first route, the overall process inverts the chirality of the starting material, L-serine, and thus provides an excellent route to the unnatural D-isomers. The alternative route starting from L-asparagine provides a shorter and high-yielding route to orthogonally protected 4-azalysine derivatives.

3.Design and Use of an Oxazolidine Silyl Enol Ether as a New Homoalanine Carbanion Equivalent for the Synthesis of Carbon-Linked Isosteres of O-Glycosyl Serine and N-Glycosyl Asparagine.

Dondoni A1, Marra A, Massi A. J Org Chem. 1999 Feb 5;64(3):933-944.

A trimethylsilyl enol ether carrying the N-Boc 2,2-dimethyloxazolidine ring was designed to serve as a synthetic equivalent of the homoalanine carbanion for the introduction of the alpha-amino acid side chain at the anomeric carbon of sugars. This new functionalized silyl enol ether was prepared in multigram scale and high enantiomeric purity starting from methyl N-Boc-L-threoninate (six steps, 49% yield). This reagent was employed in two synthetic approaches to C-glycosyl amino acids. In one approach, the BF(3).Et(2)O-promoted coupling with tetra-O-benzyl-D-galactopyranosyl trichloroacetimidate afforded the alpha-linked C-glycoside as main product (30% isolated yield), which upon treatment with tert-butyllithium was converted into the beta-linked isomer. Deoxygenation of these compounds by the Barton-McCombie method and unmasking of the glycyl moiety from the oxazolidine ring by oxidative cleavage with the Jones reagent gave the C-glycosyl serine isosteres alpha- and beta-Gal-CH(2)()-Ser.

4.High yielding selective access to spirocyclopropanated 5-oxopiperazine-2-carboxylates and 1,4-diazepane-2,5-diones from methyl 2-chloro-2-cyclopropylideneacetate.

Limbach M1, Korotkov VS, Es-Sayed M, de Meijere A. Org Biomol Chem. 2008 Oct 21;6(20):3816-22. doi: 10.1039/b809174a. Epub 2008 Aug 13.

The 2-spirocyclopropanated methyl 5-oxopiperazine-2-carboxylate and the 3-spirocyclopropanated 6-chloro-1,4-diazepane-2,5-dione could both be prepared at choice in 93 and 88% yield, respectively, from methyl 2-chloro-2-cyclopropylideneacetate () in a sequence of Michael addition of 3-benzyloxypropylamine, peptide coupling with N-Boc-glycine, Boc-group removal and cyclization. Transformation of the benzyloxypropyl side chain, peptide coupling with N-Boc-(S)-asparagine, deprotection and repeated cyclization led to the octahydro[2H]pyrazino[1,2-a]pyrazinetrione scaffold containing a rigidified mimic of a tripeptide with a DGR motif. The overall yield of after deprotection of (a total of 13 steps in 8 distinct operations) was 30%.