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Application Area

Z-L-aspartic acid

* 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-003324

CAS number

1152-61-0

Molecular Formula

C12H13NO6

Molecular Weight

267.20

IUPAC Name

(2S)-2-(phenylmethoxycarbonylamino)butanedioic acid

Synonyms

Z-L-Asp-OH; N-Carbobenzyloxy-L-Aspartic Acid

Appearance

White to off-white solid

Purity

≥ 99% (Assay)

Density

1.3276 g/cm3(rough estimate)

Melting Point

115-119 °C

Boiling Point

410.42°C (rough estimate)

Storage

Store at 2-8 °C

InChI

InChI=1S/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)/t9-/m0/s1

InChI Key

XYXYXSKSTZAEJW-VIFPVBQESA-N

Canonical SMILES

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

Z-L-aspartic acid, often abbreviated as Z-L-Asp, is a derivative of aspartic acid, an amino acid crucial to many biochemical processes. The "Z" in Z-L-aspartic acid denotes a protective group, typically used in peptide synthesis to prevent unwanted reactions. This compound is widely utilized in the synthesis of peptides and proteins due to its role in facilitating the formation of peptide bonds and protecting amino groups during chemical reactions. Z-L-aspartic acid is crucial for maintaining the stability and purity of synthesized peptides, making it an important tool in peptide chemistry and drug development.

One significant industrial application of Z-L-aspartic acid is in the pharmaceutical industry. It serves as a key intermediate in the synthesis of peptide-based drugs, including hormone analogs and enzyme inhibitors. The use of Z-L-aspartic acid in this context ensures that the peptide drugs are produced with high purity and efficacy, which is essential for their therapeutic effectiveness. The precision and efficiency provided by Z-L-aspartic acid in peptide synthesis contribute to the development of more effective and safer pharmaceutical products.

Another critical application of Z-L-aspartic acid is in the field of biotechnology, specifically in the production of recombinant proteins. The compound is used in the development of expression systems that produce high-quality proteins for research and therapeutic purposes. By facilitating the synthesis of complex peptides and proteins, Z-L-aspartic acid aids in the generation of proteins with specific functions, which are vital for various biotechnological applications, including diagnostics and treatment development.

Z-L-aspartic acid also finds use in the cosmetic industry, where it is employed in the formulation of peptide-based skincare products. Its role here is to stabilize and protect peptides that are incorporated into cosmetics, enhancing their efficacy and longevity. The inclusion of Z-L-aspartic acid in cosmetic formulations helps in developing products that can deliver targeted benefits, such as anti-aging and skin repair, by ensuring the peptides remain active and effective over time.

Lastly, Z-L-aspartic acid is utilized in the agricultural sector, particularly in the synthesis of peptide-based fertilizers and pesticides. Its role involves aiding in the creation of compounds that enhance the delivery and effectiveness of nutrients and pesticides. By improving the stability and activity of these agricultural products, Z-L-aspartic acid contributes to more efficient and sustainable agricultural practices.

1. Synthesis of aspartame precursor: alpha-L-aspartyl-L-phenylalanine methyl ester in ethyl acetate using thermolysin entrapped in polyurethane

C P Yang, C S Su Biotechnol Bioeng. 1988 Aug 20;32(5):595-603. doi: 10.1002/bit.260320504.

Cross-linked polyurethane (PU) was prepared for entrapping thermolysin. Using the immobilized thermolysin (IT), Z-L-aspartic acid (ZA) was reacted with -Lphenylalanine methyl ester (L-PM) in water-saturated ethyl acetate to give only alpha-Z-L-aspartylL-phenylalanine methyl ester (alpha-ZAPM). Ninety-four percent conversion of alpha-ZAPM was obtained for 30 h of reaction at 40 degrees C when 46 mg of enzyme was entrapped. PU support prepared from polypropylene glycol (#2000) showed better properties than from polypropylene (#1000) and polyethylene (#1000). Addition of polyol could increase the gel fraction of PU. The IT PU-ll-G-3, prepared from 1/2 mole ratio of PPG (#2000)/glycerin, gave the highest gel fraction and best swelling, and 89.0% of residual activity was obtained after four times of reuse (72 h). The stability of immobilized thermolysin was good; the activity loss resulting from degradatin and leak of enzyme in each time of reuse were found only about 2%. The kinetics of immobilized thermolysin-catalyzed condensation reaction of ZA with L-PM in water-saturated ethyl acetate was found to be first order in L-PM and the Lineweaver-Burk plot of 1/V against 1/[ZA] yields a straight line, showing that the reaction involves consecutive reactions of ZA and L-PM with the immobilized enzyme and with the ZA-immobilized enzyme complex, with the second reaction being the rate determining step.

2. Use of molecularly imprinted polymers in a biotransformation process

L Ye, O Ramström, R J Ansell, M O Månsson, K Mosbach Biotechnol Bioeng. 1999 Sep 20;64(6):650-5.

Molecularly imprinted polymers are highly stable and can be sterilised, making them ideal for use in biotransformation process. In this communication, we describe a novel application of molecularly imprinted polymers in an enzymatic reaction. The enzymatic condensation of Z-L-aspartic acid with L-phenylalanine methyl ester to give Z-L-Asp-L-Phe-OMe (Z-aspartame) was chosen as a model system to evaluate the applicability of using molecularly imprinted polymers to facilitate product formation. When the product-imprinted polymer is present, a considerable increase (40%) in product yield is obtained. Besides their use to enhance product yields, as demonstrated here, we suggest that imprinted polymers may also find use in the continuous removal of toxic compounds during biochemical reactions.

3. A new application of molecularly imprinted materials

L Ye, O Ramström, M O Månsson, K Mosbach J Mol Recognit. 1998 Winter;11(1-6):75-8. doi: 10.1002/(SICI)1099-1352(199812)11:1/63.0.CO;2-Q.

We have studied the possibility of shifting a thermodynamically unfavourable enzymatic equilibrium towards product formation via the addition of a highly specific adsorbent. The commercially interesting enzymatic condensation of Z-L-aspartic acid with L-phenylalanine methyl ester to the sweetener aspartame was chosen as the model system. Extremely stable and specific adsorbents for the product Z-L-Asp-L-Phe-OMe (Z-aspartame) were prepared using the emerging technique of molecular imprinting. A considerable increase (40%) in the yield of product was obtained when such adsorbents were present during the enzymatic reaction. The message of this investigation is that the use of such specific, sterilizable adsorbents should be considered for enzymatic processes to increase the yield. Finally, the direct isolation of a product formed by the retrieval of the adsorbents carrying the product can be envisaged, especially if the adsorbents are magnetic.