25616-33-5

Usage

Chemical Properties

White powder

InChI:InChI=1/C16H22N2O5/c1-16(2,3)23-15(22)18-12(14(21)17-10-13(19)20)9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,17,21)(H,18,22)(H,19,20)

Upstream product

• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 6000-44-8 sodium glycinate 
• 78569-23-0 3-(N-t-butoxycarbonyl-L-phenylalanyl)-1,3-thiazolidine-2-thione 
• 56-40-6 glycine 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 63-91-2 L-phenylalanine 
• 50903-54-3 N-[(1,1-dimethylethoxy)carbonyl]-L-phenylalanine pentafluorophenyl ester 
• 158840-15-4 glycine allyl ester 
• 42280-29-5 [(S)-2-tert-butoxycarbonylamino-3-phenylpropanoylamino]acetic acid benzyl ester 
• 7625-57-2 methyl 2-((2S)-2-((tert-butoxycarbonyl)amino)-3-phenylpropanamido)acetate 

Downstream Products

• 17790-88-4 Boc-Phe-NHNHPh 
• 236424-90-1 N-tert-butyloxycarbonyl-L-phenylalanyl-glycyl-L-leucine allyl ester 
• 58172-54-6 H-Phe-Gly-Leu-Met-NH₂ hydrochloride 
• 160693-35-6 Boc-Glu(OMe)-Phe-Gly-Leu-Met-NH₂ 
• 160693-33-4 Boc-Asp(OBzl)-Phe-Gly-Leu-Met-NH₂ 
• 160693-34-5 Boc-Glu(OBzl)-Phe-Gly-Leu-Met-NH₂ 
• 160693-42-5 Boc-Orn(Boc)-Glu(OMe)-Phe-Gly-Leu-Met-NH₂ 
• 160693-40-3 Boc-Orn(Boc)-Asp(OBzl)-Phe-Gly-Leu-Met-NH₂ 
• 160693-41-4 Boc-Orn(Boc)-Glu(OBzl)-Phe-Gly-Leu-Met-NH₂ 
• 960078-39-1 Nα-(tert-butyloxycarbonyl)-Nω-(3,4,5-trioctyloxyphenyl)-L-phenylalanylglycinamide 
• 1160857-15-7 methyl N-{3-[S-(N-tert-butyloxycarbonylphenylalanylglycyl)]mercapto-2-methylpropanoyl}prolinate 
• 1255743-94-2 4-(2-(2-tert-butoxycarbonylamino-3-phenylpropionylamino)acetylamino)-2,2,6,6-tetramethylpiperidin-1-oxyl 
• 1446350-55-5 N-Boc-L-Phe-Gly-L-Phe-Gly-OEt 
• 1446350-53-3 N-Boc-phenylalanine-glycine p-toluene thioester 

Relevant academic research and scientific papers

Synthesis, photophysical, photochemical, DNA cleavage/binding and cytotoxic properties of pyrene oxime ester conjugates

A new series of (E)-pyrene oxime ester conjugates of carboxylic acids including amino acids were synthesized by coupling with an environment sensitive fluorophore 1-acetylpyrene. (E)-Pyrene oxime esters exhibited strong fluorescence properties and interestingly their fluorescence properties were found to be highly sensitive to the surrounding environment. Direct irradiation of the (E)-pyrene oxime esters by UV light (≥350 nm) resulted in both the photo-Beckmann rearrangement product and products resulting from N-O bond homolysis. Photoproduct formation and their distribution were found to be solvent dependent. Further, we also showed (E)-pyrene oxime esters intercalated into DNA efficiently and photo-cleaved DNA. Finally we also showed these oxime esters can permeate cells efficiently and may cause cytotoxicity upon irradiation of light. The Royal Society of Chemistry and Owner Societies.

VISIBLE-LIGHT MEDIATED ORGANOPHOTOREDOX CATALYTIC DEUTERATION OF AROMATIC AND ALIPHATIC ALDEHYDES

Described are methods for preparing a deuterated aldehyde using with a photocatalyst and a hydrogen atom transfer agent in a H2O free solvent comprising D2O and an organic solvent under an inert gas. The methods may be used to convert a wide variety of aldehydes (e.g., aryl, alkyl, or alkenyl aldehydes) to C-1 deuterated aldehydes under mild reaction conditions.

Influence of the dipeptide linker configuration on the activity of PSMA ligands

Selective ligands of an urea-based prostate specific membrane antigen with a phenylalanine/tyrosine-based dipeptide linker and with a mingled chiral centers configuration and/or substituted aromatic fragments were prepared in seven steps by liquid- and in

Aggregation propensity of amyloidogenic and elastomeric dipeptides constituents

This study demonstrates the self-assembly of N- and C-terminal protected dipeptides Phe–Gly and Pro–Gly which were derived from amyloidogenic and elastomeric peptide sequences. These constituents afforded nanostructured supramolecular ensembles through va

π-Stacking assisted redox active peptide-gallol conjugate: Synthesis of a new generation of low-toxicity antimicrobial silver nanoparticles

In this study, we describe the rational design and synthesis of a redox-active petide-gallol conjugate and explore its application in the preparation of antimicrobial silver nanoparticles. Increase in acidity and redox activity of peptide-gallol compounds

Development of fluorescent peptide substrates and assays for the key autophagy-initiating cysteine protease enzyme, ATG4B

Abstract An efficient assay for monitoring the activity of the key autophagy-initiating enzyme ATG4B based on a small peptide substrate has been developed. A number of putative small fluorogenic peptide substrates were prepared and evaluated and optimized

Design, synthesis and preliminary evaluation of α-sulfonyl γ-(glycinyl-amino)proline peptidomimetics as matrix metalloproteinase inhibitors

A series of novel α-sulfonyl γ-(glycinyl-amino)proline peptidomimetic derivatives were designed, synthesized and assayed for their activities against matrix metalloproteinase-2 (MMP-2), aminopeptidase N (APN)/CD13 and HDACs. The results indicated that all the compounds exhibited highly selective inhibition against MMP-2 as compared with APN and HDACs. The antiproliferative activities of some compounds against SKOV3, HL60 and A549 cells were also investigated. Comparing with the control LY52, compound 12u, with excellent activity both in the enzymatic inhibition assay and cell-based assay, could be used as lead compound for the further development of MMP inhibitors.

Multigram-scale synthesis of short peptides via a simplified repetitive solution-phase procedure

(Chemical Equation Presented) A rapid repetitive solution-phase synthesis of peptides is described. The procedure involves coupling of amino acids and peptide acids, instead of the usual amino esters and peptide esters, to slight excesses of pentafluoroph

Synthesis of the palmitoylated and prenylated C-terminal lipopeptides of the human R- and N-Ras proteins

For the study of biological phenomena influenced by the R- and N-Ras proteins, characteristic peptides which embody the correct lipid modifications of their parent proteins (palmitoyl thioesters, geranylgeranyl thioethers, and farnesyl thioethers), as well as analogues thereof, may serve as efficient tools. For the construction of such acid- and base labile peptide conjugates the allyl ester was developed as C-terminal protecting group. Allyl esters are cleaved selectively and in high yields from lipidated peptides by Pd(0)-mediated allyl transfer to accepting N- or C-nucleophiles like morpholine and N,N'-dimethylbarbituric acid. This protecting group technique formed the key step in the synthesis of the characteristic S-palmitoylated and S-isoprenylated C-terminus of human R-Ras and human N-Ras proteins, as well as several analogues thereof. Deprotections are so mild that no undesired side reactions of the lipid conjugates are observed. Copyright (C) 1999 Elsevier Science Ltd.

Synthesis of substance-P C-terminal hexapeptide analogues and their biological activity. Analogues with antagonistic activity without containing D-amino acids

Analogues of the C-terminal hexapeptide of substance P have been synthesized in which each amino-acid residue was replaced by the bulky and strong lipophilic residue Asp(OBzl). The amino-acid residue of other selected places has also been replaced by Glu(