29227-88-1

Usage

Definition

ChEBI: A dipeptide composed of glycine and 5-oxo-L-proline joined by a peptide linkage.

InChI:InChI=1/C7H10N2O4/c10-5-2-1-4(9-5)7(13)8-3-6(11)12/h4H,1-3H2,(H,8,13)(H,9,10)(H,11,12)/t4-/m0/s1

Upstream product

• 22899-83-8 L-Pyroglutamylglycine ethyl ester 
• 2650-65-9 H-Gln-Gly-OH 
• 56-40-6 glycine 
• 14842-41-2 (S,S)-1,7-diazatricyclo[7.3.0.0^7,11]dodecane-2,6,8,12-tetrone 
• 934-06-5 (S)-5-oxopyrrolidine-2-carbohydrazide 

Downstream Products

• 16364-60-6 (S)-1,4-diazabicyclo[4.3.0]nonane-2,5,9-trione 

Relevant academic research and scientific papers

Five- and six-membered ring opening of pyroglutamic diketopiperazine

A variety of ring-opening reactions of pyroglutamic diketopiperazine at both the five-membered and six-membered rings is described. Mild, basic conditions facilitate nucleophilic attack by amines at the diketopiperazine carbonyls giving pyroglutamides in excellent yield. Reaction with nucleophiles under acidic conditions give bis-glutamate derivatives of 2,5-diketopiperazine (DKP). These reactions provide simple, two-step sequences to pyroglutamides and symmetrical diketopiperazines from commercial pyroglutamic acid with control of product dictated by reaction conditions, catalyst, and nucleophile.

APPLICABILITY OF GLUTAMINYL-tRNA CYCLOTRANSFERASE IN THE PEPTIDE SYNTHESIS

Peptides with amino-terminal glutamine and their derivatives on treatment with crude papain preparation, containing glutaminyl-tRNA cyclotransferase (E.C. 2.3.2.5.), are converted into the corresponding compounds with pyroglutamic acid.This enzymic cyclization does not take place with glutamic acid or its γ-derivatives.The reaction has been optimized for the preparation of pyroglutamic acid phenylhydrazide.Glutaminyl-leucine phenylhydrazide and glutaminyl-histidyl-proline amide reacted to give pyroglutamyl-leucine phenylhydrazide and TRH, respectively.Treatment of crude papain with iodoacetamide completely inhibited its activity without affecting the glutaminyl-cyclotransferase activity.