- Influence of Sulfur-Containing Diamino Acid Structure on Covalently Crosslinked Copolypeptide Hydrogels
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Biologically occurring non-canonical di-α-amino acids were converted into new di-N-carboxyanhydride (di-NCA) monomers in reasonable yields with high purity. Five different di-NCAs were separately copolymerized with tert-butyl-l-glutamate NCA to obtain covalently crosslinked copolypeptides capable of forming hydrogels with varying crosslinker density. Comparison of hydrogel properties with residue structure revealed that different di-α-amino acids were not equivalent in crosslink formation. Notably, l-cystine was found to produce significantly weaker hydrogels compared to l-homocystine, l-cystathionine, and l-lanthionine, suggesting that l-cystine may be a sub-optimal choice of di-α-amino acid for preparation of copolypeptide networks. The di-α-amino acid crosslinkers also provided different chemical stability, where disulfide crosslinks were readily degraded by reduction, and thioether crosslinks were stable against reduction. This difference in response may provide a means to fine tune the reduction sensitivity of polypeptide biomaterial networks.
- Raftery, Eric D.,Gharkhanian, Eric G.,Ricapito, Nicole G.,McNamara,Deming, Timothy J.
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p. 3547 - 3553
(2018/09/25)
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- Structure-guided design of a methyl donor cofactor that controls a viral histone H3 lysine 27 methyltransferase activity
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vSET (a viral SET domain protein) is an attractive polycomb repressive complex 2 (PRC2) surrogate to study the effect of histone H3 lysine 27 (H3K27) methylation on gene transcription, as both catalyze histone H3K27 trimethylation. To control the enzymatic activity of vSET in vivo with an engineered S-adenosyl-l-methionine (SAM) analogue as methyl donor cofactor, we have carried out structure-guided design, synthesis, and characterization of orthogonal vSET methyltransferase mutant/SAM analogue pairs using a "bump-and-hole" strategy.
- Li, Jiaojie,Wei, Hua,Zhou, Ming-Ming
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supporting information; experimental part
p. 7734 - 7738
(2012/01/13)
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- Nucleosides XI. Synthesis and antiviral evaluation of 5′-alkylthio- 5′-deoxy quinazolinone nucleoside derivatives as S-adenosyl-L-homocysteine analogs
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4-Amino-1-(β-D-ribofuranosyl)quinazolin-2-one (3) was prepared by a direct glycosylation of 4-aminoquinazolin-2-one (7) using the Vorbruggen's silylation method and provided exclusively the β-anomer. This quinazoline nucleoside and its 2′,3′-O-isopropylid
- Chien, Tun-Cheng,Chen, Chien-Shu,Yu, Fang-Hwa,Chern, Ji-Wang
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p. 1422 - 1426
(2007/10/03)
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- Chemoenzymatic Synthesis of 4-Substituted Riboses. S-(4'-Methyladenosyl)-L-homocysteine
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The synthesis of 4-C-methyl-D-ribose, 4-C-phenyl-D-ribose, D-ribose-4-d, and L-ribose derivatives as well as the title nucleoside by a chemoenzymatic strategy beginning from cyclopentadiene is described.
- Johnson, Carl R.,Esker, John L.,Zandt, Michael C. Van
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p. 5854 - 5855
(2007/10/02)
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