4-Benzyl N-carbobenzoxy-L-aspartate
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4-Benzyl N-carbobenzoxy-L-aspartate

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Category
CBZ-Amino Acids
Catalog number
BAT-003328
CAS number
3479-47-8
Molecular Formula
C19H19NO6
Molecular Weight
357.40
4-Benzyl N-carbobenzoxy-L-aspartate
IUPAC Name
(2S)-4-oxo-4-phenylmethoxy-2-(phenylmethoxycarbonylamino)butanoic acid
Synonyms
Z-L-Asp(OBzl)-OH; 4-Benzyl Hydrogen N-((Phenylmethoxy)Carbonyl)-L-Aspartate; N-Carbobenzoxy-L-Aspartic Acid 4-Benzyl Ester
Appearance
White to off-white powder
Purity
≥ 99% (assay)
Density
1.293 g/cm3
Melting Point
105-108 °C
Boiling Point
587.4°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C19H19NO6/c21-17(25-12-14-7-3-1-4-8-14)11-16(18(22)23)20-19(24)26-13-15-9-5-2-6-10-15/h1-10,16H,11-13H2,(H,20,24)(H,22,23)/t16-/m0/s1
InChI Key
VUKCNAATVIWRTF-INIZCTEOSA-N
Canonical SMILES
C1=CC=C(C=C1)COC(=O)CC(C(=O)O)NC(=O)OCC2=CC=CC=C2

4-Benzyl N-carbobenzoxy-L-aspartate is an organic compound derived from the amino acid L-aspartic acid. It is primarily used as a protective group in peptide synthesis to prevent unwanted reactions at the carboxyl or amine groups during the formation of peptide bonds. The compound’s benzyl and carbobenzoxy groups serve as temporary shields, which can later be removed under mild conditions without damaging the desired peptide sequence. Its role in peptide chemistry is crucial for ensuring precise control over complex peptide chain assembly.

One key industrial application of 4-Benzyl N-carbobenzoxy-L-aspartate is in pharmaceutical manufacturing, particularly in the synthesis of therapeutic peptides. These peptides are essential for developing drugs targeting a wide range of diseases, such as cancer, diabetes, and autoimmune disorders. The compound ensures that peptide bonds are formed in the correct sequence, allowing for the production of high-purity pharmaceuticals.

Another critical application is in biotechnology research, where the compound is used to synthesize peptide-based biomaterials. These biomaterials are employed in tissue engineering, drug delivery systems, and regenerative medicine. By facilitating the controlled formation of peptides, 4-Benzyl N-carbobenzoxy-L-aspartate aids in the development of biomaterials that can mimic natural tissue structures or deliver drugs in a targeted and sustained manner.

4-Benzyl N-carbobenzoxy-L-aspartate is also used in the agrochemical industry for the design and production of peptide-based bioactive molecules. These molecules can function as herbicides, insecticides, or fungicides, contributing to sustainable agricultural practices. The compound’s ability to ensure precise peptide synthesis is critical in developing bioactive compounds that can target specific pests or diseases without harming the environment.

Finally, in the field of cosmetics, 4-Benzyl N-carbobenzoxy-L-aspartate plays a role in the synthesis of bioactive peptides used in anti-aging products. These peptides promote collagen production, improve skin elasticity, and reduce the appearance of wrinkles. The precision in peptide assembly provided by this compound ensures the consistency and efficacy of cosmetic formulations.

1. (4S)-4-Benzyl-N-{[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]sulfon-yl}-2-oxo-1,3-oxazolidine-3-carboxamide
Malika Berredjem, Assia Allaoui, Amani Direm, Noureddine Aouf, Nourredine Benali-Cherif Acta Crystallogr Sect E Struct Rep Online. 2010 Jun 9;66(Pt 7):o1611-2. doi: 10.1107/S1600536810020866.
The title compound, C(21)H(21)N(3)O(7)S, contains an oxazolidinone ring and a sulfonamide group, both characteristic for biologically and pharrmaceutically active compounds. Both stereogenic centres reveal an S absolute configuration. The two oxazolidinone rings are in an envelope conformation with the methyl-ene carbon flap atoms deviating by 0.428 (1) and 0.364 (2) Å from the best least-square planes formed by the four other ring atoms. An intra-molecular N-H⋯O hydrogen bond contributes to the folded conformation of the mol-ecule. In the crystal, weak inter-molecular C-H⋯O inter-actions connect the mol-ecules into helices along the the twofold screw axes.
2. N-[(2Z,4Z)-4-Benzyl-idene-6-chloro-1,4-dihydro-pyrido[2,3-d][1,3]thia-zin-2-yl-idene]benzamide
Manuel A Fernandes, Demetrius C Levendis, David H Reid Acta Crystallogr Sect E Struct Rep Online. 2012 Aug 1;68(Pt 8):o2346. doi: 10.1107/S1600536812029741. Epub 2012 Jul 7.
In the crystal structure of the title compound, C(21)H(14)ClN(3)OS, mol-ecules assemble into inversion dimers via pairs of N-H⋯N hydrogen bonds involving the N-H hydrogen of the thia-zine ring and the N atom of the pyridine ring. There is a close intra-molecular contact [2.570 (2) Å] between the carbonyl O atom of the benzamide and the S atom of the puckered thia-zine ring. The title compound can exist in two tautomeric forms, viz. amino or imino. The observed structure is compatible with the imino form on the basis of observed residual electron density and the two C-N bond lengths of 1.308 (2) and 1.353 (2) Å.
3. 4-Benzyl-N-methyl-piperazine-1-carbothio-amide
Amer M Alanazi, Ali A El-Emam, Nasser R El-Brollosy, Seik Weng Ng, Edward R T Tiekink Acta Crystallogr Sect E Struct Rep Online. 2012 Mar 1;68(Pt 3):o712-3. doi: 10.1107/S1600536812005685. Epub 2012 Feb 17.
The asymmetric unit in the title thio-urea derivative, C(13)H(19)N(3)S, comprises three independent mol-ecules (A, B and C). The thio-urea groups are superimposable for the three mol-ecules, but there are significant conformational differences. Mol-ecules A and B are approximate mirror images of each other, and mol-ecule C has an inter-mediate conformation. The dihedral angles between the thio-urea groups and the phenyl rings are 52.10 (5), 63.29 (5) and 66.46 (6)° in mol-ecules A, B and C, respectively. Each independent mol-ecule self-associates into a supra-molecular chain along [100] via N-H⋯S hydrogen bonds. Mol-ecules of A and B assemble into layers four mol-ecules thick in the ac plane via C-H⋯S and C-H⋯π inter-actions. Mol-ecules of C self-assemble into layers in the ac plane via C-H⋯S inter-actions. The layers stack along the b axis with no specific inter-actions between them.
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