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Application Area

Z-D-alanine

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

Category

CBZ-Amino Acids

Catalog number

BAT-003278

CAS number

26607-51-2

Molecular Formula

C11H13NO4

Molecular Weight

223.20

IUPAC Name

(2R)-2-(phenylmethoxycarbonylamino)propanoic acid

Synonyms

Z-D-Ala-OH; (R)-2-(((Benzyloxy)Carbonyl)Amino)Propanoic Acid

Appearance

White powder

Purity

≥ 99.5% (HPLC, Chiral purity)

Density

1.161 g/cm3

Melting Point

82-87 °C

Boiling Point

212.9°C

Storage

Store at 2-8 °C

InChI

InChI=1S/C11H13NO4/c1-8(10(13)14)12-11(15)16-7-9-5-3-2-4-6-9/h2-6,8H,7H2,1H3,(H,12,15)(H,13,14)/t8-/m1/s1

InChI Key

TYRGLVWXHJRKMT-MRVPVSSYSA-N

Canonical SMILES

CC(C(=O)O)NC(=O)OCC1=CC=CC=C1

Z-D-alanine, a unique type of amino acid with diverse properties, finds various applications in the realm of biosciences. Here are the key applications illuminated with high perplexity and burstiness:

Peptide Synthesis: Central to peptide synthesis, Z-D-alanine plays a crucial role in crafting peptides particularly in generating specific stereoisomeric forms pivotal for investigating protein structure and function. The incorporation of Z-D-alanine into peptides can significantly impact their conformation and biological functionalities a fundamental process in tailoring peptides with distinct characteristics suited for both research and therapeutic endeavors.

Antibiotic Development: At the forefront of antibiotic development, Z-D-alanine serves as a foundational component in the production of specific antibiotics like vancomycin. Its exceptional stereochemistry is indispensable for the biological potency and efficacy of these antibiotics. By harnessing Z-D-alanine in antibiotic synthesis the battle against resistant bacterial strains is bolstered rendering it an invaluable asset in advancing pharmaceutical research and development efforts.

Chiral Intermediates Production: Serving as a pivotal chiral intermediate, Z-D-alanine contributes to the creation of various pharmaceuticals and agrochemicals by introducing specific chiral centers into chemical compounds thus facilitating asymmetric synthesis. This application holds significance in generating enantiomerically pure substances that may exhibit enhanced efficacy and reduced side effects compared to racemic mixtures underscoring its importance in pharmaceutical manufacturing.

Enzyme Research: The exploration of enzyme specificity and mechanisms that interact with D-amino acids is propelled by the use of Z-D-alanine in enzymatic research. By dissecting the interactions between enzymes and Z-D-alanine, scientists can unearth valuable insights into enzyme-substrate recognition and catalysis laying the groundwork for designing enzyme inhibitors and cultivating novel biocatalysts tailored for industrial applications accentuating the critical role of Z-D-alanine in enzymology and biocatalysis.

1.Synthesis of histidinoalanine: a comparison of β-lactone and sulfamidate electrophiles.

Taylor CM1, De Silva ST. J Org Chem. 2011 Jul 15;76(14):5703-8. doi: 10.1021/jo200744d. Epub 2011 Jun 14.

Previous syntheses of histidinoalanine (HAL) have led to mixtures of regioisomers and/or stereoisomers. For example, opening of N-Cbz-D-serine-β-lactone (6) with Boc-L-His-OMe (5) gave a 2:1 mixture of τ- and π-regioisomers. The sulfamidate 10, derived from N-benzyl-D-serine methyl ester (11), was reacted with Boc-L-His-OMe (5) to give the τ-HAL derivative 17 as a single isomer in 57% yield. A similarly prepared τ-HAL 19, bearing protecting groups that were all hydrogenolytically labile, led to the free bis-amino acid, τ-L-histidinyl-D-alanine (τ-4), as a salt-free standard for amino acid analysis.

2.Preparation of optically pure δ-lactones using diastereomeric resolution with amino acid as resolving agent.

Shimotori Y1, Hoshi M, Seki S, Osanai T, Okabe H, Ikeda Y, Miyakoshi T. J Oleo Sci. 2015;64(1):75-90. doi: 10.5650/jos.ess14124.

Synthesis of optically pure δ-lactones by diastereomeric resolution was investigated. Amino acid derivatives, which can be obtained at a relatively low cost, were used as resolving agents. Six optically pure δ-lactones were efficiently synthesized using Cbz-L-alanine without other expensive resolving agents. Both enantiomers of δ-lactone obtained had over 98% enantiomeric excesses. This diastereomeric resolution is very efficient for the preparation of optically pure δ-lactones.

3.Conformational ensembles of flexible beta-turn mimetics in DMSO-d6.

Koivisto JJ1, Kumpulainen ET, Koskinen AM. Org Biomol Chem. 2010 May 7;8(9):2103-16. doi: 10.1039/b921794k. Epub 2010 Mar 11.

Beta-turns play an important role in peptide and protein chemistry, biophysics, and bioinformatics. The aim of this research was to study short linear peptides that have a high propensity to form beta-turn structures in solution. In particular, we examined conformational ensembles of beta-turn forming peptides with a general sequence CBz-L-Ala-L-Xaa-Gly-L-Ala-OtBu. These tetrapeptides, APGA, A(4R)MePGA, and A(4S)MePGA, incorporate proline, (4R)-methylproline, and (4S)-methylproline, respectively, at the Xaa position. To determine the influence of the 4-methyl substituted prolines on the beta-turn populations, the NAMFIS (NMR analysis of molecular flexibility in solution) deconvolution analysis for these three peptides were performed in DMSO-d(6) solution. The NBO (natural bond orbital) method was employed to gain further insight into the results obtained from the NAMFIS analysis. The emphasis in the NBO analysis was to characterize remote intramolecular interactions that could influence the backbone-backbone interactions contributing to beta-turn stability.

4.Design and synthesis of a tetradentate '3-amine-1-carboxylate' ligand to mimic the metal binding environment at the non-heme iron(II) oxidase active site.

Dungan VJ1, Ortin Y, Mueller-Bunz H, Rutledge PJ. Org Biomol Chem. 2010 Apr 7;8(7):1666-73. doi: 10.1039/b921934j. Epub 2010 Feb 4.

Non-heme iron(II) oxidases (NHIOs) catalyse a diverse array of oxidative chemistry in Nature. As part of ongoing efforts to realize biomimetic, iron-mediated C-H activation, we report the synthesis of a new 'three-amine-one-carboxylate' ligand designed to complex with iron(II) and mimic the NHIO active site. The tetradentate ligand has been prepared as a single enantiomer in nine synthetic steps from N-Cbz-L-alanine, pyridine-2,6-dimethanol and diphenylamine, using Seebach oxazolidinone chemistry to control the stereochemistry. X-Ray crystal structures are reported for two important intermediates, along with variable temperature NMR experiments to probe the hindered interconversion of conformational isomers of several key intermediates, 2,6-disubstituted pyridine derivatives. The target ligand and an N-Cbz-protected precursor were each then complexed with iron(II) and tested for their ability to promote alkene dihydroxylation, using hydrogen peroxide as the oxidant.