Late-stage C(sp2)–H and C(sp3)–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling

C–H glycosylations of complex amino acids and peptides were accomplished through the assistance of triazole peptide-isosteres. The palladium-catalyzed glycosylation provided access to complex C-glycosides and fluorescent-labeled glycoamino acids.

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Palladium-Catalyzed Carbonylative Cyclization of Amines via γ-C(sp3)–H Activation: Late-Stage Diversification of Amino Acids and Peptides

ACS Catalysis ◽

10.1021/acscatal.6b01987 ◽

2016 ◽

Vol 6 (10) ◽

pp. 6868-6882 ◽

Cited By ~ 66

Author(s):

Elier Hernando ◽

Julia Villalva ◽

Ángel Manu Martínez ◽

Inés Alonso ◽

Nuria Rodríguez ◽

...

Keyword(s):

Amino Acids ◽

Late Stage ◽

Palladium Catalyzed

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Sequential C-Selective Difluoromethylation/Pd-Catalyzed Decarboxylative Protonation: An Efficient Access to Tertiary Difluoromethylated Scaffolds

10.26434/chemrxiv.8091314 ◽

2019 ◽

Author(s):

Nicolas Duchemin ◽

Roberto Buccafusca ◽

Marc Daumas ◽

Vincent Ferey ◽

Stellios Arseniyadis

Keyword(s):

Drug Development ◽

Late Stage ◽

Efficient Access ◽

Palladium Catalyzed ◽

General Method

We report here a general method that allows a highly straightforward access to tertiary difluoromethylated compounds. The strategy relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and an unprecedented palladium-catalyzed decarboxylative protonation. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.<br>

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ChemInform Abstract: N-Boc-α-tosylsarcosine Ethyl Ester: An α-Amido Sulfone for the Regio- and Stereoselective Synthesis of Protected γ,δ-Unsaturated N-Methyl-α-amino Acids by Palladium-Catalyzed Nucleophilic Substitution.

ChemInform ◽

10.1002/chin.199806228 ◽

2010 ◽

Vol 29 (6) ◽

pp. no-no

Author(s):

D. A. ALONSO ◽

A. COSTA ◽

C. NAJERA

Keyword(s):

Amino Acids ◽

Nucleophilic Substitution ◽

Ethyl Ester ◽

Stereoselective Synthesis ◽

Palladium Catalyzed

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ChemInform Abstract: Elaboration of the Side Chain of α-Amino Acids Containing a Vinyl Iodide by Palladium-Catalyzed Coupling.

ChemInform ◽

10.1002/chin.199426237 ◽

2010 ◽

Vol 25 (26) ◽

pp. no-no

Author(s):

G. T. CRISP ◽

P. T. GLINK

Keyword(s):

Amino Acids ◽

Side Chain ◽

Vinyl Iodide ◽

Palladium Catalyzed

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Stereoselective Synthesis of β-Alkylated α-Amino Acids via Palladium-Catalyzed Alkylation of Unactivated Methylene C(sp3)–H Bonds with Primary Alkyl Halides

Journal of the American Chemical Society ◽

10.1021/ja406484v ◽

2013 ◽

Vol 135 (32) ◽

pp. 12135-12141 ◽

Cited By ~ 251

Author(s):

Shu-Yu Zhang ◽

Qiong Li ◽

Gang He ◽

William A. Nack ◽

Gong Chen

Keyword(s):

Amino Acids ◽

Stereoselective Synthesis ◽

Alkyl Halides ◽

Palladium Catalyzed

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Insights into genome recoding from the mechanism of a classic +1-frameshifting tRNA

Nature Communications ◽

10.1038/s41467-020-20373-z ◽

2021 ◽

Vol 12 (1) ◽

Author(s):

Howard Gamper ◽

Haixing Li ◽

Isao Masuda ◽

D. Miklos Robkis ◽

Thomas Christian ◽

...

Keyword(s):

Amino Acids ◽

Conformational Change ◽

Molecular Mechanism ◽

Late Stage ◽

Anticodon Loop ◽

Pairing Mechanism ◽

Extra Nucleotide ◽

In Cells

AbstractWhile genome recoding using quadruplet codons to incorporate non-proteinogenic amino acids is attractive for biotechnology and bioengineering purposes, the mechanism through which such codons are translated is poorly understood. Here we investigate translation of quadruplet codons by a +1-frameshifting tRNA, SufB2, that contains an extra nucleotide in its anticodon loop. Natural post-transcriptional modification of SufB2 in cells prevents it from frameshifting using a quadruplet-pairing mechanism such that it preferentially employs a triplet-slippage mechanism. We show that SufB2 uses triplet anticodon-codon pairing in the 0-frame to initially decode the quadruplet codon, but subsequently shifts to the +1-frame during tRNA-mRNA translocation. SufB2 frameshifting involves perturbation of an essential ribosome conformational change that facilitates tRNA-mRNA movements at a late stage of the translocation reaction. Our results provide a molecular mechanism for SufB2-induced +1 frameshifting and suggest that engineering of a specific ribosome conformational change can improve the efficiency of genome recoding.

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Plasma albumin synthesis during neonatal development of the rat

Biochemical Journal ◽

10.1042/bj1020760 ◽

1967 ◽

Vol 102 (3) ◽

pp. 760-762 ◽

Cited By ~ 16

Author(s):

R. W. Wise ◽

I. T. Oliver

Keyword(s):

Amino Acids ◽

Specific Antibody ◽

Late Stage ◽

Normal Adult ◽

Albumin Synthesis ◽

Plasma Albumin ◽

Pregnant Rat ◽

Liver Slices ◽

Parenchymal Cells ◽

Very High

1. Liver slices were incubated with (14)C-labelled amino acids. Albumin was isolated from the slices by precipitation with specific antibody and the incorporated radioactivity measured. 2. The rate of synthesis was seen to be equal in liver slices from adult and late-stage foetal rats. 3. Synthesis was very high in the pregnant rat (three times the normal adult value) and in the 5-15-day post-natal rat (twice the normal adult value). 4. The post-natal increase may be due to the disappearance of haemopoietic tissue and its replacement by active parenchymal cells.

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