2766-17-8

Usage

Uses

Used in Pharmaceutical Industry:
Z-VAL-GLY-OET is used as a building block for the synthesis of peptide and protein-based drugs, facilitating the development of new therapeutic agents with specific functions and properties.
Used in Biochemical Research:
Z-VAL-GLY-OET is used as a research tool to study the effects of valine and glycine on peptide and protein structures and functions, aiding in the understanding of their roles in biological processes.
Used in Drug Delivery Systems:
Z-VAL-GLY-OET is employed in the design and development of drug delivery systems, potentially enhancing the efficacy and bioavailability of peptide and protein-based drugs.
Used in Precursor for Pharmaceutical Compounds:
Z-VAL-GLY-OET serves as a precursor in the synthesis of new pharmaceutical compounds, offering a versatile starting point for the creation of innovative treatments for various medical conditions.

InChI:InChI=1/C17H24N2O5/c1-4-23-14(20)10-18-16(21)15(12(2)3)19-17(22)24-11-13-8-6-5-7-9-13/h5-9,12,15H,4,10-11H2,1-3H3,(H,18,21)(H,19,22)

Upstream product

• 1149-26-4 (S)-N-(benzyloxycarbonyl)valine 
• 623-33-6 glycine ethyl ester hydrochloride 
• 459-73-4 GlyOEt*HCl 
• 1685-33-2 N-[(benzyloxy)carbonyl]-D-valine 
• 3496-11-5 2,5-dioxopyrrolidin-1-yl (2S)-2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate 
• 19411-70-2 N-tert-butyl-N'-methylcarbodiimide 
• 55546-43-5 N,N′-diisopropylcarbodiimide 
• 54647-77-7 N-[(benzyloxy)carbonyl]-L-valine, compound with dicyclohexylamine (1:1) 
• 133010-20-5 Cbz-Val-F 
• 70082-89-2 (S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid 6-chloro-benzotriazol-1-yl ester 
• 137283-66-0 N-(Z-valine)phthalimide 
• 53666-01-6 (S)-2-Benzyloxycarbonylamino-3-methyl-butyric acid (1S,7R)-3,5-dioxo-4-aza-tricyclo[5.2.1.0^2,6]dec-8-en-4-yl ester 
• 53666-01-6 N-(benzyloxycarbonyl)-L-valine N-hydroxy-5-norbornene-2,3-dicarboximide ester 
• 33857-66-8 N-benzyloxycarbonyl-L-valine 2-pyridylthiol ester 

Downstream Products

• 22221-75-6 N-(N-benzyloxycarbonyl-L-valyl)-glycine 
• 33477-44-0 Cbz-valylglycyl hydrazide 
• 686-43-1 valylglycine 
• 1027906-73-5 C₄₈H₇₁N₇O₁₃ 
• 1027166-82-0 ((S)-2-{(S)-2-[(S)-2-((S)-2-{(R)-2-[(S)-2-tert-Butoxycarbonylamino-3-(4-hydroxy-phenyl)-propionylamino]-propionylamino}-3-phenyl-propionylamino)-3-carbamoyl-propionylamino]-3-methyl-butyrylamino}-3-methyl-butyrylamino)-acetic acid ethyl ester 
• 147424-48-4 Z-Asp(OtBu)-Val-Val-Gly-OEt 
• 147424-49-5 Z-Asn-Val-Val-Gly-OEt 
• 147424-39-3 Z-Val-Val-Gly-OEt 
• 264236-36-4 ethyl N-(o-azidobenzoyl)-L-valylglycinate 
• 264236-41-1 (3S)-1-acetyl-4-(o-azidobenzoyl)-3-isopropyl-2,5-piperazinedione 
• 264236-26-2 (6S)-1-(o-azidobenzoyl)-6-iso-propylpiperazine-2,5-dione 

Relevant academic research and scientific papers

Tandem deprotection/coupling for peptide synthesis in water at room temperature

A tandem deprotection/coupling sequence is reported for solution-phase peptide synthesis in water under micellar catalysis conditions using the designer surfactant TPGS-750-M. Cbz deprotection followed by peptide coupling in the presence of COMU and 2,6-lutidine afforded polypeptides containing up to 10 amino acid residues. A broad scope characterizes this new technology. No epimerization has been detected. The associated E Factors, as a measure of "greenness" and known to be extremely high for peptide couplings, have been reduced to less than 10 due to the step-economy and minimal amounts of organic solvent needed for product extraction.

Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters

Metal-free direct amidation of peptidyl thiol esters with α-amino acid esters in the presence of bis(trimethylsilyl) acetamide (BSA) has been developed. This general method provides convenient access to N-protected peptides in good yields under mild condi

A new method for the synthesis of carboxamides and peptides using 1,1′-carbonyldioxydi[2(1H)-pyridone] (CDOP) in the absence of basic promoters

Various carboxamides or peptides are synthesized from the corresponding carboxylic acids and amines or α-amino acids using 1,1′-carbonyldioxydi[2(1H)-pyridone]. The reaction proceeds in the absence of basic promoters such as triethylamine or 4-(dimethylamino)pyridine, therefore, the undesired racemization does not occur at all in the segment coupling producing Z-Gly-Phe-Val-OMe and Z-Phe-Val-Ala-OMe.

N, N′-Carbonyldisaccharin: A new condensing agent for the synthesis of amides, esters and peptides

A new, easy to handle and efficient condensing agent N,-N′ -carbonyldisaccharin 2 has been readily synthesised by the reaction of saccharin 1 and trichloromethyl chloroformate in toluene. The condensing agent 2 is demonstrated to be useful for the synthesis of amides, esters and dipeptides under mild conditions in a one-pot procedure.

A convenient method for the preparations of carboxamides and peptides by using di(2-pyridyl) carbonate and O,O′-di(2-pyridyl) thiocarbonate as dehydrating reagents

Preparations of carboxamides and peptides are performed in high yields from free carboxylic acids and amines by dehydration condensation using di(2-Pyridyl) carbonate (DPC) or O,O′-Di(2-Pyridyl) thiocarbonate (DPTC) in the presence of a catalytic amount of 4-(dimethylamino)pyridine (DMAP). The formation of 2-Pyridyl esters, key intermediates of the reaction, from carboxylic acids by using DPC proceeded faster than by using DPTC; therefore, the former carbonate is more efficiently employed in the above condensation reactions.

A New Route toward 4-Substituted Pyrazino[2,1-b]quinazoline-3,6-dione Systems. Total Synthesis of Glyantrypine

Treatment of sodium N-(o-azidobenzoyl)aminoacylglycinates 8 with acetic anhydride afforded 1-acetyl-4-(o-azidobenzoyl)-2,5-piperazinediones 7, with complete retention of the stereochemistry. The intramolecular aza Wittig reactions of compounds 7 in the pr

New system for peptide synthesis using N-acylpyrazoles

New system of peptide synthesis was described. The extension of one amino acid unit on the peptide chain was constituted from only 2 reaction steps, the conversion from esters to the corresponding N-acylpyrazoles and the subsequent aminolysis with amino esters. This new system was distinctive from the conventional peptide synthesis, which was consisted of 3 steps of the deprotection, the activation and the condensation. Moreover, the key intermediate N-acylpyrazoles exhibited the excellent properties of high sensitivity and separability for the chiral column on HPLC using the UV detector.

Formation of N-Acylureas During the Peptide Coupling with the Use of Unsymmetrical Carbodiimides

A study was concucted to determine the effect of alkyl groups of N,N'-dialkylcarbodiimides on the formation of N-acylureas during the peptide coupling.The use of carbodiimides of the structure Bu-t-N=C=N-R, where R=Me, Et and Pr-i, resulted in the formation of two isomeric N-acylureas.The proportion of the two compounds in the mixture was determined by 1H NMR spectroscopy and confirmed by chromatographic isolation.It was established that it is the least hindered O-acylurea nitrogen atom that attacks intramolecularly the amino acid activated by the unsymmetrical carbodiimide to form the major rearrangement product. Key words: carbodiimide, coupling reagent, peptide synthesis

New Carbodiimides for Peptide Synthesis

Three carbodiimides: N,N'-dicyclopentylcarbodiimide, N,N'-di-2-methylcyclohexylcarbodiimide and N,N'-dimenthylcarbodiimide were prepared and used for activation of the carboxyl group in peptide coupling reactions.Several model reactions were carried out t

Synthesis of a new saccharin derivative (BID-SPy) and its utilization as a condensing reagent in the preparation of dipeptides

A new saccharin derivative, thiopyridyl-benzisothiazole 1,1-dioxide (BID-SPy, 2), has been prepared by the reaction of BID-Cl (1) and 2-mercaptopyridine, and utilized as a coupling reagent in the synthesis of amides and N-protected dipeptides.