2483-51-4

Usage

Uses

Used in Pharmaceutical Research:
Z-ALA-ALA-OME is used as a substrate for studying enzyme activity and peptide synthesis, facilitating the understanding of the biological and biochemical functions of amino acids and peptides.
Used in Biochemical Studies:
Z-ALA-ALA-OME is employed as a model compound to explore the interactions and mechanisms of enzymes and peptides, contributing to the advancement of knowledge in biochemistry.
Used in Drug Development:
Z-ALA-ALA-OME is utilized in the development of pharmaceuticals, particularly for the synthesis of peptide-based drugs, due to its unique structure and properties that aid in the study of enzyme activity and peptide synthesis.
Used in Academic Research:
Z-ALA-ALA-OME is used as a research tool in academic settings to investigate the fundamental aspects of amino acid and peptide chemistry, providing insights into their roles in biological systems.

Upstream product

• 10065-72-2 L-Alanine methyl ester 
• 1142-20-7 N-Cbz-Ala 
• 67-56-1 methanol 
• 16012-70-7 benzyloxycarbonyl-L-alanyl-L-alanine 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 186581-53-3 diazomethane 
• 210840-42-9 N-(Benzyloxycarbonyl)alanine (3,5-di-tert-butyl-4-hydroxyphenyl)ester 
• 4132-86-9 N-benzyloxycarbonylalanine 
• 65638-93-9 N-Carbobenzoxy-L-alanin-kohlensaeureaethylesteranhydrid 
• 133010-19-2 (S)-N-cbz-alanoyl fluoride 
• 501-53-1 benzyl chloroformate 
• 22221-78-9 Z-Ala-Ala-OMe 
• 122751-37-5 Z-Ala-OPyCl 
• 26607-52-3 Cbz-Ala-OH*DCHA 

Downstream Products

• 2483-52-5 benzyl ((S)-1-(((S)-1-hydrazinyl-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)carbamate 
• 177657-10-2 (2S)-2-[N-(Benzyloxycarbonyl-(S)-alanyl-(S)-alanyl)amino]-4-methylpentan-1-ol 
• 178910-89-9 Z-Ala-Ala-Pheol 
• 16012-70-7 benzyloxycarbonyl-L-alanyl-L-alanine 
• 261769-08-8 C₂₄H₃₀N₆O₅ 
• 3886-07-5 Cbz-L-ala-L-ala-Cbz 
• 5845-61-4 cyclo(L-Ala-L-Ala) 
• 95205-40-6 mononitrosated benzoxycarbonylalanylalanine methyl ester 
• 95205-39-3 dinitrosated benzoxycarbonylalanylalanine methyl ester 
• 87043-02-5 Z-L-Ala-ψ(CSNH)-L-Ala-OMe 
• 41036-19-5 L-alanyl-alanine methylester hydrochloride 
• 5625-46-7 (+/-)-cis-3,6-dimethyl-piperazine-2,5-dione 

Relevant academic research and scientific papers

HIGH OXIDATION STATE TRANSITION METAL CARBOXYLATES AS ACYLATING AGENTS

The formation of amide bonds from the reaction of metal carboxylates with amines was observed for the first time; complexes for titanium(IV), zirconium(IV) and tantalum(V) were investigated.

Optimization and anti-cancer properties of fluoromethylketones as covalent inhibitors for ubiquitin C-terminal hydrolase L1

The deubiquitinating enzyme (DUB) UCHL1 is implicated in various disease states including neurodegenerative disease and cancer. However, there is a lack of quality probe molecules to gain a better understanding on UCHL1 biology. To this end a study was carried out to fully characterize and optimize the irreversible covalent UCHL1 inhibitor VAEFMK. Structure-activity relationship studies identified modifications to improve activity versus the target and a full cellular characterization was carried out for the first time with this scaffold. The studies produced a new inhibitor, 34, with an IC50 value of 7.7 μM against UCHL1 and no observable activity versus the closest related DUB UCHL3. The molecule was also capable of selectively inhibiting UCHL1 in cells and did not demonstrate any discernible off-target toxicity. Finally, the molecule was used for initial probe studies to assess the role of UCHL1 role in proliferation of myeloma cells and migration behavior in small cell lung cancer cells making 34 a new tool to be used in the biological evaluation of UCHL1.

Metal-free approach for hindered amide-bond formation with hypervalent iodine(iii) reagents: application to hindered peptide synthesis

A new bio-inspired approach is reported for amide and peptide synthesis using α-amino esters that possess a potential activating group (PAG) at the ester residue. To activate the ester functionality under mild metal-free conditions, we exploited the facile dearomatization of phenols with hypervalent iodine(iii) reagents. Using a pyridine-hydrogen fluoride complex, highly reactive acyl fluoride intermediates can be successfully generated, thereby allowing for the smooth formation of sterically hindered amides and peptides from bulky amines and α-amino esters, respectively.

Design, synthesis, and in vitro evaluation of aza-peptide aldehydes and ketones as novel and selective protease inhibitors

Aza-peptide aldehydes and ketones are a new class of reversible protease inhibitors that are specific for the proteasome and clan CD cysteine proteases. We designed and synthesised aza-Leu derivatives that were specific for the chymotrypsin-like active si

Investigation of permeation of theophylline through skin using selected piperazine-2,5-diones

Transdermal administration of drugs that penetrate, in this case directly into the blood circulation, has many advantages and is promising for many drugs thanks to its easy application and good patient compliance. (S)-8-Methyl-6,9-diazaspiro[4.5]decan-7,10-dione (alaptide), has been studied as a potential chemical permeation enhancer. Based on its structure, four selected piperazine-2,5-diones were synthesized by means of multi-step synthetic pathways. All the compounds were investigated on their ability to enhance the permeation of the model drug theophylline from the hydrophilic medium propylene glycol:water (1:1). In vitro experiments were performed using vertical Franz diffusion cells at constant temperature 34 ± 0.5 ?C and using full-thickness pig (Sus scrofa f. domestica) ear skin. Withdrawn samples were analyzed by RP-HPLC for determination of the permeated amount of theophylline. All the compounds were applied in ratio 1:10 (w/w) relative to the amount of theophylline. One hour after application, the permeated amount of theophylline from formulations with alaptide and (3S,6S)-3,6-dimethylpiperazine-2,5-dione, was ca. 15- and 12-fold higher, respectively, than from the formulation without the tested compounds. Despite the enhancement ratio of both enhancers in a steady state was ca. 2.3, the pseudo-enhancement ratio in the time range from 1 to 3 h was 4.4. These enhancement ratios indicate that the compounds are able to enhance the permeation of agents through the skin; however, the short-term application of both compound formulations seems to be more advantageous. In addition, the screening of the cytotoxicity of all the prepared compounds was performed using three cell lines, and the compounds did not show any significant toxic effect.

Legumain Activated Doxorubicin Derivative as well as Preparation Method and Application Thereof

The present invention discloses doxorubicin derivatives for targeted activation by Legumain, its preparation method and use. The doxorubicin derivatives are obtained by condensation between the amino group of compound A and the carboxyl group of compound B and have the following structure: compounds A and B have the following structures, respectively: wherein R3 in compound B is Leu or absent; R4 is any one amino acid selected from the group consisting of Ala and Thr; R5 is any one amino acid selected from the group consisting of Ala, Thr and Asn; R6 is wherein n=1-20; or wherein R7 is substituted or unsubstituted, linear or branched, saturated or unsaturated C1-C20 fatty hydrocarbon, or substituted or unsubstituted C6-C20 aromatic hydrocarbon. The doxorubicin derivatives of the present invention are specifically tumor-targeted and have a long in vivo metabolic half-life, as compared with doxorubicin. They exhibit an efficient and safe anti-tumor effect and could be used to prepare an anti-tumor drug.

Substrate-directed lewis-acid catalysis for peptide synthesis

A Lewis-acid-catalyzed method for the substrate-directed formation of peptide bonds has been developed, and this powerful approach is utilized for the new "remote" activation of carboxyl groups under solvent-free conditions. The presented method has the following advantages: (1) the high-yielding peptide synthesis uses a tantalum catalyst for any amino acids; (2) the reaction proceeds without any racemization; (3) the new substrate-directed chemical ligation using the titanium catalyst is applicable to convergent peptide synthesis. These advantages overcome some of the unresolved problems in classical peptide synthesis.

Legumain Activated Doxorubicin Derivative as well as Preparation Method and Application Thereof

The present invention discloses doxorubicin derivatives for targeted activation by Legumain, its preparation method and use. The doxorubicin derivatives are obtained by condensation between the amino group of compound A and the carboxyl group of compound B and have the following structure: compounds A and B have the following structures, respectively: wherein R3 in compound B is Leu or absent; R4 is any one amino acid selected from the group consisting of Ala and Thr; R5 is any one amino acid selected from the group consisting of Ala, Thr and Asn; R6 is wherein n=1-20; or wherein R7 is substituted or unsubstituted, linear or branched, saturated or unsaturated C1-C20 fatty hydrocarbon, or substituted or unsubstituted C6-C20 aromatic hydrocarbon. The doxorubicin derivatives of the present invention are specifically tumor-targeted and have a long in vivo metabolic half-life, as compared with doxorubicin. They exhibit an efficient and safe anti-tumor effect and could be used to prepare an anti-tumor drug.

SPECIFICALLY ACTIVATED MICROMOLECULAR TARGET COUPLING BODY IN TUMOR MICROENVIRONMENT AND USE THEREOF

Provided are an anticancer compound comprising a cleavable linker specifically activated in a tumor microenvironment, and use thereof. The anticancer compound is represented by the following formula, wherein, R1 is a normal functional group or a protection group; R2 is Ala, Thr, Val or Ile; R3 is Ala, Val or Asn; R4 is a drug group linked via a hydroxyl group or an amino group; and the general formula of the drug is R4H. The anticancer compound is only activated at a local portion of a tumor, thus avoiding the defect of immune system damage of a traditional chemotherapeutic drug, and promoting tumor immunization by removing a tumor immunosuppression cell. The anticancer compound or pharmaceutical composition thereof is jointly used with immunotherapy, thus improving the effect of treating the tumor, and effectively inhibiting tumor metastasis and osseous metastasis.

3-Azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate), a new reagent for the synthesis of the N-protected amino acid-ASUD ester

A new reagent, 3-azaspiro[5,5]undecan-2,4-dioxo-3-yl diphenyl phosphate (ASUD-diphenyl phosphate) is described for the synthesis of N-protected amino acid-ASUD esters which are active esters useful in the synthesis of peptides. This compound was synthesized by reacting N-hydroxy-3-azaspiro[5,5]undecane-2,4-dione (HO-ASUD) with diphenyl chlorophosphate in the presence of a base at room temperature and was obtained in high yields. The ASUD-diphenyl phosphate reagent reacts with N-protected amino acids under mild conditions to give the corresponding ASUD active esters, while preserving the enantiomeric purity of the amino acid. The new reagent is a stable crystalline compound and eliminates the need for DCC, a potent skin allergen, used previously for the synthesis of N-protected amino acid-ASUD ester.