3079-63-8

Usage

Uses

Z-Gly-Ala-OH can be used to treat fungal infection.

InChI:InChI=1/C13H16N2O5/c1-9(12(17)18)15-11(16)7-14-13(19)20-8-10-5-3-2-4-6-10/h2-6,9H,7-8H2,1H3,(H,14,19)(H,15,16)(H,17,18)

Upstream product

• 56-41-7 L-alanin 
• 62632-23-9 (S)-tert-butyl 2-(2-(((benzyloxy)carbonyl)amino)acetamido)propanoate 
• 3082-75-5 L-Alanine ethyl ester 
• 1138-80-3 N-(Benzyloxycarbonyl)glycine 
• 2899-60-7 Cbz-Gly-ONSuc 
• 1738-86-9 Z-Gly-ONp 
• 4824-12-8 N-(benzyloxycarbonyl)glycine pentachlorophenyl ester 
• 16859-24-8 Benzyloxycarbonylamino-acetic acid 3-ethylcarbamoyl-2-hydroxy-phenyl ester 
• 10466-61-2 (2S)-amino-4-methylpentanamide hydrochloride 
• 252846-37-0 Z-Gly-L-Ala-O-carbamoylmethyl 
• 501-53-1 benzyl chloroformate 
• 173459-80-8 benzyl [2?(1H?benzo[d][1,2,3]triazol?1?yl)?2?oxoethyl]carbamate 
• 1145-81-9 ethyl 2-(benzyloxycarbonylamino)ethanoate 
• 5680-83-1 N-(benzyloxycarbonyl)glycine hydrazide 

Downstream Products

• 3695-73-6 glycyl-L-alanine 
• 102096-37-7 {[(S)-1-(6-Methoxy-quinolin-8-ylcarbamoyl)-ethylcarbamoyl]-methyl}-carbamic acid benzyl ester 
• 22849-49-6 H-Gly-L-Ala-L-Leu-OH 
• 23013-50-5 H-Gly-D-Ala-L-Leu-OH 
• 15112-71-7 N-benzyloxycarbonylglycyl-L-alanyl-L-phenylalanine methyl ester 
• 7801-73-2 N-carbobenzoxyglycyl-L-alanylglycine benzyl ester 
• 22849-48-5 Z-Gly-S-Ala-S-Leu-OBzl 
• 24569-24-2 Z-Gly-D-Ala-Leu-OBzl 
• 4066-24-4 Z-Gly-Ala-OBzl 
• 252846-37-0 Z-Gly-L-Ala-O-carbamoylmethyl 
• 102610-21-9 Z-Gly-L-Ala-L-Ala-OMe 
• 803706-39-0 N-(diazoacetyl)-L-alanine-N-[(1S)-2-tert-butoxy-2-oxo-1-phenylethyl]amide 
• 803706-41-4 glycyl-L-alanine-N-[(1S)-2-tert-butoxy-2-oxo-1-phenylethyl]amide 
• 175918-15-7 (S)-2-({(R)-1-[(S)-2-(2-Benzyloxycarbonylamino-acetylamino)-propionylamino]-2-phenyl-ethyl}-methoxy-phosphinoyloxy)-3-phenyl-propionic acid 3-pyridin-4-yl-propyl ester 

Relevant academic research and scientific papers

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.

Rational Design of Small Peptides for Optimal Inhibition of Cyclooxygenase-2: Development of a Highly Effective Anti-Inflammatory Agent

Among the small peptides 2-31, (H)Gly-Gly-Phe-Leu(OMe) (30) reduced prostaglandin production of COX-2 with an IC50 of 60 nM relative to 6000 nM for COX-1. The 5 mg kg-1 dose of compound 30 rescued albino mice by 80% from capsaicin-induced paw licking and recovered it by 60% from carrageenan-induced inflammation. The mode of action of compound 30 for targeting COX-2, iNOS, and VGSC was investigated by using substance P, l-arginine, and veratrine, respectively, as biomarkers. The interactions of 30 with COX-2 were supported by isothermal calorimetry experiments showing a Ka of 6.10 ± 1.10 × 104 M-1 and ΔG of -100.3 kJ mol-1 in comparison to a Ka 0.41 × 103 ± 0.09 M-1 and ΔG of -19.2 ± 0.06 kJ mol-1 for COX-1. Moreover, compound 30 did not show toxicity up to a 2000 mg kg-1 dose. Hence, we suggest peptide 30 as a highly potent and promising candidate for further development into an anti-inflammatory drug.

Gabapentin hybrid peptides and bioconjugates

Synthetic approaches to gabapentin bioconjugates that overcome the tendency of gabapentin to cyclize into its γ-lactam are studied. Gabapentin was converted by N-acylation at its N-terminus into di-, tri-, and tetrapeptides (L-Ala-Gbp, L-Val-Gbp, L-Ala-L-Phe-Gbp, Gly-L-Ala-β-Ala-Gbp). Carboxyl-activated Boc-protected gabapentin was used to N-, O-, and S-acylate small peptides and hormones to give conjugates that could also provide prodrugs containing conformationally constrained gabapentin units.

α-chymotrypsin-catalysed segment condensations via the kinetically controlled approach using carbamoylmethyl esters as acyl donors in organic media

The superiority of the carbamoylmethyl ester as an acyl donor for the α-chymotrypsin-catalysed segment condensations via the kinetically controlled approach is demonstrated in several model systems carried out in organic media with low water content. Furthermore, this approach is successfully applied to the construction of the Leu-enkephalin sequence via a 4 + 1 segment coupling.

Superiority of the carbamoylmethyl ester as an acyl donor for the protease-catalyzed kinetically controlled peptide synthesis in organic media: Application to segment condensations

The superiority of the carbamoylmethyl ester as an acyl donor for the α-chymotrypsin-catalyzed kinetically controlled peptide synthesis was demonstrated in several segment condensations carried out in organic media with low water content. Then this approach was successfully applied to the construction of the Leuenkephalin sequence via the 4 + 1 segment condensation.

Enzymatische Synthese von Peptiden und Ras-Lipopeptiden unter Verwendung des Cholinesters als loeslichkeitsvermittelnder Schutz- und Aktivierungsgruppe

Keywords: Cholinesterase; Enzymkatalyse; Peptidsynthesen; Ras-Proteine

Zur Totalsynthese von Human-Sekretin

The synthesis of the heptacosapeptide amide with the primary structure of Human-secretin is described.For this purpose 7 fragments were designed, i.e.H-Gly-Leu-Val-NH2 , Z-Arg(Z2)-Leu-Leu-Gln-OH , Z-Arg(Z2)-Leu-Gln-OH , Z-Arg(Z2)-Glu(OtBu)-Gly-Ala-OH , Z-Arg(Z2)-Leu-OH , Z-Thr(tBu)-Ser(tBu)-Glu(OtBu)-Leu-Ser(tBu)-OH , Adoc-His(Adoc)-Ser(tBu)-Asp(OtBu)-Gly-Thr(tBu)-Phe-OH ; these fragments were consequently assembled to the overall protected total sequence using the Wuensch/Weygand-method with dicyclohexylcarbodiimide.After deprotection by exposure to trifluoroacetic acid in presence of 1,2-ethanediol and water as scavenger, the islated crude product was purified by column chromatography on CM-Sepharose, fast flow.This synthesized Human-secretin showed the full biological activity in comparison to Porcine-secretin. Key words: Gastrointestinal hormone; Human-secretin: synthetic peptide factors.

SYNTHESIS OF MESOIONIC TRIAZOLOPYRIDINE. III. APPLICATIONS OF N-ACYL MESOIONIC TRIAZOLOPYRIDINES AS ACYLATING REAGENTS.

Utility of N-acyl mesoionic triazolopyridines as acylating reagents was investigated concerning with peptide synthesis. Several dipeptides and N-alkoxycarbonyl amino acids were prepared by use of these reagents.