1152-61-0

Basic information

• Product Name: N-Carbobenzyloxy-L-aspartic acid
• Synonyms: Z-ASPARTIC ACID;Z-ASP;Z-L-ASPARTIC ACID;Z-L-ASP-OH;L-ASPARTIC ACID, N-[(PHENYLMETHOXY)CARBONYL]-;CBZ-ASP-OH;CBZ-L-ASP;CBZ-L-ASPARTIC ACID
• CAS NO: 1152-61-0
• Molecular Formula: C₁₂H₁₃NO₆
• Molecular Weight: 267.23
• EINECS: 214-568-4
• Product Categories: Protected Amino Acids;Amino Acid Derivatives;PROTECTED AMINO ACID & PEPTIDES;Aspartic acid [Asp, D];Z-Amino Acids and Derivatives;Amino Acids;Amino Acids (N-Protected);Biochemistry;Cbz-Amino Acids;Chiral Compounds;Z-Amino acid series
• Mol File: 1152-61-0.mol

Chemical Properties

• Melting Point: 117-119 °C(lit.)
• Boiling Point: 410.42°C (rough estimate)
• Flash Point: 239.7 °C
• Appearance: White/Fine Crystalline Powder
• Density: 1.3276 (rough estimate)
• Vapor Pressure: 9.58E-10mmHg at 25°C
• Refractive Index: 9.5 ° (C=7, AcOH)
• Storage Temp.: 2-8°C
• Solubility: almost transparency in Methanol
• PKA: 3.75±0.23(Predicted)
• BRN: 2336722
• CAS DataBase Reference: N-Carbobenzyloxy-L-aspartic acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-Carbobenzyloxy-L-aspartic acid(1152-61-0)
• EPA Substance Registry System: N-Carbobenzyloxy-L-aspartic acid(1152-61-0)

Safety Data

• Hazard Codes: Xi,Xn
• Statements: 36/37/38-20/21/22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 1152-61-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Carbobenzyloxy-L-aspartic acid is used as an intermediate in the synthesis of various pharmaceutical compounds due to its ability to protect the carboxyl group of L-Aspartic acid during chemical reactions. This protection allows for the selective functionalization of other groups on the molecule, which is essential for the development of new drugs and therapeutic agents.
Used in Biochemical Research:
In the field of biochemical research, N-Cbz-L-aspartic acid is utilized as a reagent for studying the properties and functions of L-Aspartic acid. Its role in the biosynthesis of other amino acids and its ability to increase membrane conductance of mammalian neurons make it a valuable tool for understanding the complex processes within the central nervous system.
Used in Drug Delivery Systems:
Similar to gallotannin, N-Cbz-L-aspartic acid can be employed in the development of novel drug delivery systems. Its protective nature allows for the creation of carriers that can enhance the delivery, bioavailability, and therapeutic outcomes of various pharmaceutical compounds, particularly those targeting the central nervous system.
Used in the Synthesis of Amino Acid Derivatives:
N-Carbobenzyloxy-L-aspartic acid is also used as a starting material for the synthesis of various amino acid derivatives. These derivatives can have altered properties and functions, making them suitable for specific applications in the pharmaceutical, biotechnological, and chemical industries.

InChI:InChI=1/C12H13NO6/c14-10(15)6-9(11(16)17)13-12(18)19-7-8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,18)(H,14,15)(H,16,17)/p-2/t9-/m0/s1

Upstream product

• 56-84-8 L-Aspartic acid 
• 501-53-1 benzyl chloroformate 
• 33605-72-0 N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester 
• 4515-21-3 N-benzyloxycarbonylaspartic acid 
• 4515-23-5 N-benzyloxycarbonyl-L-aspartic acid anhydride 
• 35909-93-4 dimethyl (2S)-2-[(phenylmethoxy)carbonylamino]-butane-1,4-dioate 
• 100-59-4 phenylmagnesium chloride 
• 2398-37-0 3-methoxyphenyl bromide 
• 109-65-9 1-bromo-butane 
• 3160-47-2 N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester 

Downstream Products

• 13795-73-8 L-aspartic acid di-tert-butyl ester 
• 68013-17-2 CbzNH-L-Asp(NMe₂)-OH 
• 3160-47-2 N-(benzyloxycarbonyl)-L-aspartic acid 4-methyl ester 
• 4668-42-2 (S)-2-benzyloxycarbonylamino-succinic acid 1-methyl ester 
• 112681-73-9 (S)-2-Benzyloxycarbonylamino-succinic acid bis-(2-oxo-propyl) ester 
• 135841-16-6 (R)-3-benzyloxycarbonyl-5-oxo-4-oxazolidinoneacetic acid 
• 1026688-17-4 C₂₅H₂₉N₃O₇ 
• 75443-62-8 benzyl N-[(3R)-2,5-dioxotetrahydrofuran-3-yl]carbamate 
• 4515-23-5 N-benzyloxycarbonyl-L-aspartic acid anhydride 
• 35739-00-5 benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate 
• 1159497-10-5 C₂₂H₃₇NO₆Si₂ 
• 127949-86-4 N-benzyloxycarbonyl-L-asparatic acid diallyl ester 
• 1196043-42-1 CbzNH-L-Asp-Gly-L-His-D-Pro-Aib-L-His-Gly-L-His-NH₂ 
• 33605-72-0 N-carbobenzyloxy-L-aspartyl-L-phenylalanine methyl ester 

Relevant articles and documents

Syntheses of Polypeptides by Hidrogenolysis of N-Benzyloxycarbonyl-Amino Acid Anhydrides

When anhydrides of N-benzyloxycarbonyl-DL-aspartic acid (Z-DL-Asp), Z-L-Asp, N-Z-DL-glutamic acid (Z-DL-Glu), Z-L-Glu and N-Z-3-aminoglutaric acid (Z-β-Agl) were hydrogenolyzed in N,N-dimethylformamide (DMF), polypeptides were obtained in high yields.Hydrogenolyses of Z-DL-Glu and Z-L-Glu in dioxane gave pyroglutamic acid.

On the racemisation of aspartic anhydride during its preparation

Due to the possible differentiation of both carboxyl groups, N-protected aspartic anhydride is a useful starting material in synthesis. However, most methods published in the literature for its formation lead to partial racemisation, which is generally not mentioned. Herein we report a comparison between the main methods published, with accurate measurements of the enantiomeric purity of this compound.

Economical synthesis of tert-butyl (S)-3-aminopyrrolidine-1-carboxylate from L-aspartic acid

3-Aminopyrrolidine building block was used as the intermediate for many pharmaceutically active substances. Starting from L-aspartic acid, optically active (S)-tert-butyl-3-aminopyrrolidine-1-carboxylate was synthesized, and the reaction conditions were optimized in each step. The procedure of each step was discussed in detail and could be useful for the industrial preparation. This process was featured by readily available starting material, mild reaction conditions, easy work-up, and economy.

Regioselective opening of N-Cbz glutamic and aspartic anhydrides with carbon nucleophiles

Depending on the experimental conditions, aspartic and glutamic anhydrides can be opened regioselectively with Grignard reagents, thus giving access to different isomers of chiral amino-ketoesters.

Antifungal dipeptides incorporating an inhibitor of homoserine dehydrogenase

The antifungal activity of 5-hydroxy-4-oxo-l-norvaline (HONV), exhibited under conditions mimicking human serum, may be improved upon incorporation of this amino acid into a dipeptide structure. Several HONV-containing dipeptides inhibited growth of human pathogenic yeasts of the Candida genus in the RPMI-1640 medium, with minimal inhibitory concentration values in the 32 to 64?μg?mL?1 range. This activity was not affected by multidrug resistance that is caused by overexpression of genes encoding drug efflux proteins. The mechanism of antifungal action of HONV dipeptides involved uptake by the oligopeptide transport system, subsequent intracellular cleavage by cytosolic peptidases, and inhibition of homoserine dehydrogenase by the released HONV. The relative transport rates determined the anticandidal activity of HONV dipeptides.

Environmentally Benign CO2-Based Copolymers: Degradable Polycarbonates Derived from Dihydroxybutyric Acid and Their Platinum-Polymer Conjugates

(S)-3,4-Dihydroxybutyric acid ((S)-3,4-DHBA), an endogenous straight chain fatty acid, is a normal human urinary metabolite and can be obtained as a valuable chiral biomass for synthesizing statin-class drugs. Hence, its epoxide derivatives should serve as promising monomers for producing biocompatible polymers via alternating copolymerization with carbon dioxide. In this report, we demonstrate the production of poly(tert-butyl 3,4-dihydroxybutanoate carbonate) from racemic-tert-butyl 3,4-epoxybutanoate (rac-tBu 3,4-EB) and CO2 using bifunctional cobalt(III) salen catalysts. The copolymer exhibited greater than 99% carbonate linkages, 100% head-to-tail regioselectivity, and a glass-transition temperature (Tg) of 37 °C. By way of comparison, the similarly derived polycarbonate from the sterically less congested monomer, methyl 3,4-epoxybutanoate, displayed 91.8% head-to-tail content and a lower Tg of 18 °C. The tert-butyl protecting group of the pendant carboxylate group was removed using trifluoroacetic acid to afford poly(3,4-dihydroxybutyric acid carbonate). Depolymerization of poly(tert-butyl 3,4-dihydroxybutanoate carbonate) in the presence of strong base results in a stepwise unzipping of the polymer chain to yield the corresponding cyclic carbonate. Furthermore, the full degradation of the acetyl-capped poly(potassium 3,4-dihydroxybutyrate carbonate) resulted in formation of the biomasses, β-hydroxy-γ-butyrolacetone and 3,4-dihydroxybutyrate, in water (pH = 8) at 37 °C. In addition, water-soluble platinum-polymer conjugates were synthesized with platinum loading of 21.3-29.5%, suggesting poly(3,4-dihydroxybutyric acid carbonate) and related derivatives may serve as platinum drug delivery carriers.

Synthesis of models of the BC ring systems of MPC1001 and MPC1001F

Piperazinedione 13, representing the BC rings of the anti-prostate cancer fungal metabolite MPC1001, was prepared by a route in which a sulfur-stabilized carbanion derived from 22 cyclizes onto the terminal ester of the pendant chain attached to N1. Another model, 14, was synthesized by cyclization of an α-ketoamide nitrogen onto an ester; 14 represents the BC rings of MPC1001F.

Synthesis and anticonvulsant evaluation of (R)-and (S)-3-carbobenzyloxy- amino-1-oxysuccinimides

A series of (R)-and (S)-3-carbobenzyloxy-amino-1-oxysuccinimides (5a-d) [(S)-3-carbobenzyloxy-amino-1-benzoyloxysuccinimde, (R)-3-carbobenzyloxy-amino- 1-acetyloxysuccinimde, (R)-3-carbobenzyloxy-amino-1,4-nitrobenzoyloxysuccinimde, (R)-3-carbobenzyloxyamino-1,4-fluorobenzoyloxysuccinimde] were synthesized and investigated their anticonvulsant activities in maximal electric shock seizure test and pentylenetetrazole induced seizure test.

A PREPARATION METHOD OF SITAGLIPTIN

The present invention relates to a preparation method of sitagliptin, and more particularly, to a method of preparing sitagliptin using L-aspartic acid having a (R)-beta amino acid structure by mild amide formation, by the use of industrially applicable halo isopropylmagnesium, and by removal of amine protecting group using Pd/C and H2 and carbonyl reduction using reducing agent.

Total synthesis of tryprostatins A and B

Three distinct synthetic routes to the 2-prenyl tryptophan core skeleton of tryprostatins and their total syntheses are described. The strategies include a traditional gramine-mediated coupling reaction, Fuerstner indole synthesis, and our radical-mediated indole synthesis from o-alkenylphenyl isocyanide. The establishment of reliable conditions for the radical-mediated construction of indoles via a low-temperature radical initiator V-70 (2,2′-azobis(4- methoxy-2,4-dimethylvaleronitrile)) led to the highly efficient syntheses of tryprostatins A and B.