158599-00-9Relevant articles and documents
Azide reduction during peptide cleavage from solid support - The choice of thioscavenger?
Schneggenburger, Philipp E.,Worbs, Brigitte,Diederichsen, Ulf
, p. 10 - 14 (2010)
Peptide azides acquired growing impact because of application in bioconjugation via 'click chemistry' or Staudinger ligation. Furthermore, there are many methods established in organic synthesis addressing the reduction of azides to amines, but no observation of a reductive transformation of peptide azides during SPPS cleavage was yet reported. In the present study, the reduction of peptide azides during SPPS cleavage was investigated depending on the choice of thioscavenger, reacting as reductive species. First observed for short PNA/peptide conjugates the occurring extensive side reaction was also validated for one of the applied azide amino acid building blocks and was further investigated by applying different cleavage cocktails to a series of peptides varying in hydrophobicity and position of the azide moiety in the oligomer sequence. Copyright
NOVEL CYCLIC PEPTIDES AND USES THEREOF
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Page/Page column 76; 77, (2018/02/28)
Novel cyclic peptide GHRP-6 analogs of formula (I): (I) or pharmaceutically acceptable esters or salts thereof, are described. These cyclic peptide GHRP-6 analogs may be used for modulating CD36 activity, for example for the treatment of CD36-related dise
Strategy for "Detoxification" of a cancer-derived histone mutant based on mapping its interaction with the methyltransferase PRC2
Brown, Zachary Z.,Müller, Manuel M.,Jain, Siddhant U.,Allis, C. David,Lewis, Peter W.,Muir, Tom W.
supporting information, p. 13498 - 13501 (2015/02/02)
The histone methyltransferase PRC2 plays a central role in genomic stability and cellular development. Consequently, its misregulation has been implicated in several cancers. Recent work has shown that a histone H3 mutant, where the PRC2 substrate residue Lys27 is replaced by methionine, is also associated with cancer phenotypes and functions as an inhibitor of PRC2. Here we investigate the mechanism of this PRC2 inhibition through kinetic studies and photo-cross-linking. Efficient inhibition is dependent on (1) hydrophobic lysine isosteres blocking the active site, (2) proximal residues, and (3) the H3 tail forming extensive contacts with the EZH2 subunit of PRC2. We further show that naturally occurring post-translational modifications of the same H3 tail, both proximal and distal to K27M, can greatly diminish the inhibition of PRC2. These results suggest that this potent gain of function mutation may be "detoxified by modulating alternate chromatin modification pathways.
Intramolecular cyclization assistance for fast degradation of ornithine-based poly(ester amide)s
De Gracia Lux, Caroline,Olejniczak, Jason,Fomina, Nadezda,Viger, Mathieu L.,Almutairi, Adah
, p. 3783 - 3790 (2013/09/02)
Inspired by the spontaneous cyclization of ornithine in peptides, polyesters containing protected ornithine (Orn) side chains along the backbone were synthesized and shown to degrade rapidly upon deprotection through intramolecular cyclization. A new ornithine-based poly(ester amide) PEA 1 and a lysine-based control PEA 2, both bearing the light-sensitive protecting group o-nitrobenzyl alcohol (ONB), were synthesized. Tert-butyl carbamate (Boc)-protected versions 1-Boc and 2-Boc were also synthesized for proof of concept. GPC confirmed that 1-Boc degrades over 40 times faster than 2-Boc following deprotection into the designed intramolecular cyclization products. Finally, TEM visualization of particles made from 1 encapsulating iron oxide nanoparticles reveals complete disruption of nanoparticles and release of payload within a day upon UV irradiation. Copyright
Use of p-nitrobenzyloxycarbonyl (pNZ) as a permanent protecting group in the synthesis of Kahalalide F analogs
López, Pilar E.,Isidro-Llobet, Albert,Gracia, Carolina,Cruz, Luis J.,García-Granados, Andrés,Parra, Andrés,álvarez, Mercedes,Albericio, Fernando
, p. 7737 - 7741 (2007/10/03)
p-Nitrobenzyloxycarbonyl (pNZ) is used for the permanent protection of ornithine in the synthesis of derivatives of the anti-tumor cyclodepsipeptide Kahalalide F that contain acid labile residues.
A novel fluorescence sensing system using a photochromism-based assay (P-CHROBA) technique for the detection of target proteins
Tomizaki, Kin-Ya,Mihara, Hisakazu
, p. 2732 - 2740 (2007/10/03)
In the post-genomic era a number of biological technologies, including protein-detecting microarrays which can detect molecular interactions based on changes in fluorescence intensity, have been developed to investigate complicated protein functions and n
