4526-93-6

Basic information

• Product Name: Z-SER-GLY-OET
• Synonyms: Z-SER-GLY-OET;Z-L-SERYL-L-GLYCINE ETHYL ESTER;((S)-2-BENZYLOXYCARBONYLAMINO-3-HYDROXY-PROPIONYLAMINO)-ACETIC ACID ETHYL ESTER;N-(Benzyloxycarbonyl)serylglycine ethyl ester;N-Cbz-L-Ser-Gly-OEt;Z-L-Ser-Gly-OEt;(S)-ethyl 2-(2-(benzyloxycarbonylamino)-3-hydroxypropanamido)acetate;CBZ-Ser-Gly-OEt
• CAS NO: 4526-93-6
• Molecular Formula: C₁₅H₂₀N₂O₆
• Molecular Weight: 324.33
• EINECS: 1533716-785-6
• Mol File: 4526-93-6.mol
• Article Data: 7

Chemical Properties

• Appearance: /Solid
• Storage Temp.: -15°C
• CAS DataBase Reference: Z-SER-GLY-OET(CAS DataBase Reference)
• NIST Chemistry Reference: Z-SER-GLY-OET(4526-93-6)
• EPA Substance Registry System: Z-SER-GLY-OET(4526-93-6)

Safety Data

• Hazardous Substances Data: 4526-93-6(Hazardous Substances Data)

Usage

General Description

Z-SER-GLY-OET, also known as Z-Serine-glycine-ethyl ester, is a chemical compound used in peptide synthesis and biochemical research. It is a derivative of serine and glycine, two amino acids that are essential building blocks of proteins. The "Z" in the name indicates the presence of a protecting group on the serine, which is commonly used to prevent undesired reactions during peptide synthesis. Z-SER-GLY-OET is often utilized in the creation of peptide-based pharmaceuticals and in the study of protein structure and function. Its unique properties make it valuable in the field of biochemistry and biotechnology.

Upstream product

• 26582-86-5 benzyl (1S)-2-hydrazino-1-(hydroxymethyl)-2-oxoethylcarbamate 
• 1145-80-8 N-(benzyloxycarbonyl)-L-serine 
• 459-73-4 GlyOEt*HCl 
• 623-33-6 glycine ethyl ester hydrochloride 
• 1676-76-2 Z-Ser(t-Bu)-Gly-OEt 
• 23161-27-5 N-(benzyloxycarbonyl)-L-serine ethyl ester 
• 81187-75-9 Z-Ser-OMpt 
• 1676-75-1 N-benzyloxycarbonyl-O-t-butyl-L-serine 
• 133010-28-3 Z-Ser(t-Bu)-F 
• 1676-81-9 N-benzyloxycarbonyl-L-serine methyl ester 
• 91586-86-6 ZSer, triethylammonium salt 

Downstream Products

• 30735-20-7 N-benzyloxycarbonylserylglycine 
• 33092-52-3 Z-Ser-Gly-hydrazide 
• 95930-73-7 N-Benzyloxycarbonyl-hydroxyglycyl-glycin-aethylester 
• 2418-62-4 Benzyloxycarbonyl-L-seryl-glycinamid 
• 135924-33-3 Z-Gly(OAc)-Gly-OEt 
• 621-84-1 O-benzyl carbamate 
• 95930-64-6 N-benzyloxycarbonyl-N'-ethoxycarbonylmethyloxamide 
• 95930-70-4 N-benzyloxycarbonyl-O-<2-benzyloxycarbonylamino-N-(ethoxycarbonylmethyl)malonamoyl>serylglycine ethyl ester 
• 55477-82-2 Z-ΔAla-Gly-OEt 
• 28130-08-7 (N-benzyloxycarbonyl-α-hydroxy)glycyl-Gly-OEt 
• 1491-68-5 Z-Ser(Tos)-Gly-OEt 
• 16675-95-9 N-benzyloxycarbonyl-L-seryl=>glycyl=>-L-glutamic acid diethyl ester 
• 687-63-8 L-Ser-Gly 
• 96635-26-6 Benzyloxycarbonyl-dehydroalanyl-glycin 

Relevant articles and documents

Diphenyl (2,3-dihydro-2-thioxo-3-benzoxazolyl)phosphonate: A new, reactive condensing agent for the synthesis of amides, esters, peptides, and β-lactams via condensation

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Synthesis and Characterisation of some New Diazopeptides

The synthesis of eight new diazopeptides by aprotic diazotisation with N2O4 is described for glycylglycine, triglycine, pentaglycine, L-leucylglycine and the ethyl esters of L-leucylglycine, L-alanylglycine, L-serylglycine and L-threonylglycine.The diazo derivatives (7) - (10) of the parent peptides are isolated as calcium salts.The UV-vis., IR, 1H NMR and MS properties of the new diazopeptides are reported together with those for the diazo derivative of glycylglycine ethyl ester and glycylglycinamide.

Peptide Synthesis with Benzo- and Naphthosultones

6-Nitro- and 6,8-dinitronaphth-1,2-oxathiole S,S-dioxides (7b and 7c) have been prepared from the parent naphthosultone 7a and compared with 5-nitrobenz-3H-1,2-oxathiole S,S-dioxide (1b) as coupling reagents for peptide synthesis.Nucleophilic attack of a carboxylate salt on these strained five-membered sultones leads to activated esters 3 and 9 which rapidly react with amines (except in the case of 9c).The rate constant for the formation of ester 9b is higher than that of 3b.Amides or peptides are formed in slightly better yields with the naphthosultone 7b than with the benzosultone 1b.The naphthosultones are also preferred over the benzosultones from the point of view of amount of 5(4H)-oxazolone formation from N-benzoyl amino acids and the degree of racemization.However the rate of alkaline hydrolysis of 7b is slower than that of 1b.All these results may be rationalized by a better intramolecular acyl transfer reaction in the more rigid mixed anhydride intermediate 8b.There is no dependence on in the rate equation for aminolysis of esters 3b and 9b by benzylamine in THF, acetonitrile, or DMF and the aminolysis is probably anchimerically assisted by a neighbouring S=O group.Esters 3b are more selective acylating agents for primary amino groups in the presence of secondary ones than esters 9b and this observation is exploited in a synthesis of maytenine by selective acylation of spermidine.