90711-56-1

Usage

Uses

Used in Biochemical Research:
N-[(Prop-2-en-1-yl)oxy]carbonylglycine, ([(Prop-2-en-1-yl)oxy]carbonylamino)acetic acid is used as a research compound for studying the effects of structural modifications on the properties and functions of glycine and its derivatives. The introduction of the prop-2-en-1-yl and carbonyl groups allows for the investigation of their impact on protein structure, enzyme activity, and other biochemical processes.
Used in Pharmaceutical Development:
In the pharmaceutical industry, N-[(Prop-2-en-1-yl)oxy]carbonylglycine, ([(Prop-2-en-1-yl)oxy]carbonylamino)acetic acid is used as a potential therapeutic agent or as a building block for the synthesis of novel drugs. The unique structural features of these compounds may offer advantages in terms of selectivity, potency, and pharmacokinetics, making them valuable for the development of new medications.
Used in Organic Synthesis:
N-[(Prop-2-en-1-yl)oxy]carbonylglycine, ([(Prop-2-en-1-yl)oxy]carbonylamino)acetic acid is used as a synthetic intermediate or a reagent in organic synthesis. The presence of the prop-2-en-1-yl and carbonyl groups provides opportunities for further functionalization and the formation of complex organic molecules with diverse applications, such as agrochemicals, dyes, and materials.
Further research is being conducted to explore the properties and potential uses of N-[(Prop-2-en-1-yl)oxy]carbonylglycine, ([(Prop-2-en-1-yl)oxy]carbonylamino)acetic acid, with the aim of fully understanding their capabilities and harnessing their potential in various industries.

Upstream product

• 98426-77-8 N-Alloc-Gly-OEt 
• 56-40-6 glycine 
• 2937-50-0 Allyl chloroformate 
• 115491-93-5 diallyl dicarbonate 
• 1235983-30-8 N-(allyloxycarbonyloxy)picolinimidoyl cyanide 
• 114416-17-0 allyl 1H-benzo[d][1,2,3]triazole-1-carboxylate 
• 61-90-5 L-leucine 

Downstream Products

• 145147-55-3 Aloc-Gly-Phe-OtBu 
• 220369-83-5 alloc-Gly-Phe 
• 208655-87-2 C₃₇H₄₈N₇O₂₀P 
• 187737-37-7 propene 
• 56-40-6 glycine 
• 100138-70-3 N-allyloxycarbonyl-glycine-(N'-phenyl-hydrazide) 
• 1185653-96-6 (3S,5S)-3-(2-tert-butoxycarbonylaminoethyl)-5-(allyloxycarbonylaminomethyl)-1-(3,5-dichlorobenzyll)-1,4-diazepan-2-one 
• 1185653-93-3 (S)-9-fluorenylmethyl 10-(3,5-dichlorobenzyl)-2,2-dimethyl-4,9,13,16-tetraoxo-3,17-dioxa-5,10,15-triazaiscos-19-en-8-ylcarbamate 

Relevant academic research and scientific papers

The Total Chemical Synthesis and Biological Evaluation of the Cationic Antimicrobial Peptides, Laterocidine and Brevicidine

Antimicrobial resistance is a significant threat to public health systems worldwide, prompting immediate attention to develop new therapeutic agents with novel mechanisms of action. Recently, two new cationic non-ribosomal peptides (CNRPs), laterocidine and brevicidine, were discovered from Brevibacillus laterosporus through a global genome-mining approach. Both laterocidine and brevicidine exhibit potent antimicrobial activity toward Gram-negative bacteria, including difficult-to-treat Pseudonomas aeruginosa and colistin-resistant Escherichia coli, and a low risk of resistance development. Herein, we report the first total syntheses of laterocidine and brevicidine via an efficient and high-yielding combination of solid-phase synthesis and solution-phase macrolactamization. The crucial depsipeptide bond of the macrolactone rings of laterocidine and brevicidine was established on-resin between the side-chain hydroxy group of Thr9 with Alloc-Gly-OH or Alloc-Ser(tBu)-OH, respectively. A conserved glycine residue within the lactone macrocycle is exploited for the initial immobilization onto the hyper acid-labile 2-chlorotrityl chloride resin, subsequently enabling an efficient solution-phase macrocyclization to yield laterocidine and brevicidine in 36% and 10% overall yields, respectively (with respect to resin loading). A biological evaluation against both Gram-positive and Gram-negative bacteria demonstrated that synthetic laterocidine and brevicidine possessed a potent and selective antimicrobial activity toward Gram-negative bacteria, in accordance with the isolated compounds.

A Lasso-Inspired Bicyclic Peptide: Synthesis, Structure and Properties

The chemical synthesis of a bicycle inspired by the natural lasso peptide sungsanpin using a combination of solid-phase and in-solution chemistries is described. The bicyclic-derived topoisomer was designed by introducing a covalent linkage between the ri

Total Synthesis of the Post-translationally Modified Polyazole Peptide Antibiotic Goadsporin

The structurally unique polyazole antibiotic goadsporin contains six heteroaromatic oxazole and thiazole rings integrated into a linear array of amino acids that also contains two dehydroalanine residues. An efficient total synthesis of goadsporin is repo

Benzotriazole reagents for the syntheses of Fmoc-, Boc-, and Alloc-protected amino acids

Stable Fmoc-, Boc-, and Alloc-benzotriazoles react with various amino acids including unprotected serine and glutamic acid, in the presence of triethylamine at 20° as reagents to introduce -amino protecting groups to afford Fmoc-, Boc-, and Alloc-protected amino acids (77-94%) free of dipeptide and tripeptide impurities. Fmoc-, and Alloc-Gly-Gly-OH dipeptides were prepared in 90% yields by N-acylation of glycylglycine with Fmoc- and Alloc-benzotriazoles in the presence of triethylamine. Synthesized N-protected amino acids were greater than 99% pure, analyzed by HPLC. Georg Thieme Verlag Stuttgart - New York.

Oxime carbonates: Novel reagents for the introduction of fmoc and alloc protecting groups, free of side reactions

Fmoc and Alloc protecting groups represent a consistent alternative to classical Boc protection in peptide chemistry. The former was established in the last decades as the α-amino protecting group of choice, whereas the latter allows a fully orthogonal protection strategy with Fmoc and Boc. Usually, the introduction of the Fmoc and Alloc moieties takes place through their halogenoformates, azides, or activated carbonates. This rather simple reaction is accompanied by several side reactions, specially the formation of Fmoc/Alloc dipeptides and even tripeptides. The present work describes new promising Fmoc/Alloc-oxime reagents, which are easy to prepare, stable, and highly reactive crystalline materials that afford almost: contaminant-free Fmoc/Alloc-amino acids in high yields by following a conventional procedure. Amongst the Fmoc-oxime derivatives, the N-hydroxypicolimmidoyl cyanide derivative (N-([(9H-fluoren-9-yl)methoxy]carbonyloxy}picolinimidoyl cyanide) gave the best results for the preparation of Fmoc-Gly-OH, which is the most predisposed to give side reactions. The same Alloc-oxime analogue afforded the preparation of Alloc-Gly-OH in good yield, purity, and extremely low dipeptide formation, as analyzed by reverse-phase HPLC and NMR spectroscopy.

One-pot preparation of N-carbamate protected amino acids via the azide

A convenient and efficient method for the preparation of fluorenylmethyloxycarbonyl (Fmoc) and allyloxycarbonyl (Alloc) amino acids is proposed. This method is particularly attractive due to the fact that the reaction sequence Fmoc/Alloc-chloride to Fmoc/Alloc-azide to Fmoc/Alloc-amino acid can readily be carried out in one pot. A further advantage is the minimization of byproducts, which are easily removed during the workup. Most important, this strategy minimizes the formation of dipeptides that are difficult to remove by crystallization. Thus, Fmoc and Alloc amino acids are obtained in high yield (60-90%) and purity as evidenced by thin-layer chromatography, reversed-phase high-performance liquid chromatography, mass spectrometry, and nuclear magnetic resonance.

Stereocontrolled synthesis of piperidine-condensed tricyclic carbapenems (5-azatrinems) and their antibacterial activities

Stereocontrolled synthesis of tricyclic carbapenem (5-azatrinem) derivatives 4, in which a piperidine ring is condensed to the carbapenem skeleton, was achieved. The pivotal tricyclic intermediate 2, allyl (8S,9R,10S)-5-(tert-butoxycarbonyl)-10-[(R)-1-(tert- butyldimethylsilyloxy)ethyl)-11-oxo-1,5-diazatricyclo[7.2.0.03,8]undec-2- ene-2-carboxylate, was synthesized starting from an acetoxyazetidinone chiron 6 in a practical manner based on a C-C bond formation reaction between 6 and piperidinone-ester 5, palladium-catalyzed de(allyloxy)carbonylation of 7b and Wittig-type cyclization via an oxalimide 9. Selective deprotection of the N- Boc group of 2 was found to proceed smoothly by treatment with trimethylsilyl trifluoromethanesulfonate and 2,6-lutidine to give the amino compound 3, whose functionalization on the nitrogen atom to derivatives 10 followed by deprotection led to various 5-azatrinem acids 4. These compounds showed potent in vitro activities against gram-positive and gram-negative bacteria.

Cathepsin B-sensitive dipeptide prodrugs. 1. A model study of structural requirements for efficient release of doxorubicin

A series of lysosomal protease-sensitive peptides attached to doxorubicin (DOX) was prepared as model substrates for internalizing anticancer immunoconjugates and potential antimetastasis prodrugs. Rates of cathepsin B-mediated release of free drug was measured for each, and human plasma stabilities for representative examples.

Crystalline aminomethyl compound

The invention relates to (5R,6S)-2-aminomethyl-6-[(1R)-1-hydroxyethyl]-2-penem-3-carboxylic acid in crystalline form and a process for the manufacture thereof. The substance is suitable for treating infectious diseases.

DIALLYL DICARBONATE. A CONVENIENT REAGENT FOR THE SYNTHESIS OF ALLYL CARBAMATES

Diallyldicarbonate was prepared and used for the amino protection of various compounds including amino acids, amino sugars and nucleosides.