Reduction of amide carbonyl group and formation of modified amino acids and dipeptides

2015 ◽  
Vol 56 (16) ◽  
pp. 2062-2066 ◽  
Author(s):  
M.L. Di Gioia ◽  
E.L. Belsito ◽  
A. Leggio ◽  
V. Leotta ◽  
E. Romio ◽  
...  
Keyword(s):  
Amino Acids ◽  
Carbonyl Group ◽  
Amide Carbonyl ◽  
Amide Carbonyl Group

Access to α,α-Difluoro-γ-amino Acids by Nickel-Catalyzed Reductive Aryldifluoroacetylation of N-Vinylacetamide

Synlett ◽  
2020 ◽  
Author(s):  
Xingang Zhang ◽  
Qing-Wei Zhao ◽  
Zhi-Fang Yang ◽  
Xia-Ping Fu
Keyword(s):  
Amino Acids ◽  
Protein Engineering ◽  
Carbonyl Group ◽  
Organometallic Reagents ◽  
Peptide Chemistry ◽  
Rapid Access ◽  
Aryl Iodides ◽  
Amide Carbonyl ◽  
Amide Carbonyl Group ◽  
Potential Applications

AbstractA nickel-catalyzed reductive aryldifluoroacetylation of N-vinylacetamide with ethyl chloro(difluoro)acetate and aryl iodides is described. This chelating amide carbonyl group-assisted strategy provides rapid access to a variety of protected α,α-difluoro-γ-amino acids that might have potential applications in peptide chemistry and protein engineering. An advantage of this method is its synthetic simplicity, with no preparation of organometallic reagents.

Efficient synthesis of N-butadiene substituted oxindole derivatives

2018 ◽  
Vol 5 (23) ◽  
pp. 3460-3463
Author(s):  
Chao Li ◽  
Wei-Huan Li ◽  
Lin Dong
Keyword(s):  
Carbonyl Group ◽  
Efficient Method ◽  
Efficient Synthesis ◽  
Amide Carbonyl ◽  
Amide Carbonyl Group

A novel rhodium(iii)-catalyzed amide carbonyl group directed alkenylation reaction between oxindoles and alkenes has been reported, which provides an efficient method for the synthesis of valuable and versatile functionalized N-(2E,4Z)-butadiene substituted oxindole derivatives.

Deoxygenative Hydroboration of Carboxamides: A Versatile and Selective Synthetic Approach to Amines

2021 ◽  
Author(s):  
Andrey Y. Khalimon
Keyword(s):  
Carbonyl Group ◽  
Thermodynamic Stability ◽  
Synthetic Approach ◽  
Amide Carbonyl ◽  
Amide Carbonyl Group ◽  
High Thermodynamic Stability

Deoxygenative reduction of amides is considered as an attractive method for preparation of synthetically valuable amines. However, the low electrophilicity of the amide carbonyl group, high thermodynamic stability and kinetic...

scholarly journals Enzymatically-stable oxetane-based dipeptide hydrogels

2018 ◽  
Vol 54 (14) ◽  
pp. 1793-1796 ◽  
Author(s):  
Laura McDougall ◽  
Emily R. Draper ◽  
Jonathan D. Beadle ◽  
Michael Shipman ◽  
Piotr Raubo ◽  
...  
Keyword(s):  
Carbonyl Group ◽  
Amide Carbonyl ◽  
Amide Carbonyl Group ◽  
Oxetane Ring

A new Fmoc-protected dipeptide incorporating an oxetane ring as a surrogate for the amide carbonyl group is an effective gelator.

Solvent effects on the conformations of ortho-substituted acetanilides

1968 ◽  
Vol 46 (15) ◽  
pp. 2589-2592 ◽  
Author(s):  
Ian D. Rae
Keyword(s):  
Hydrogen Bond ◽  
Carbonyl Group ◽  
Aromatic Ring ◽  
Solvent Effects ◽  
Ortho Position ◽  
Polar Solvents ◽  
Amide Carbonyl ◽  
Amide Carbonyl Group ◽  
Intramolecular Hydrogen ◽  
Deshielding Effect

In acetanilides bearing nitro, halogen, alkoxyl, or carboxyl substituents in the ortho position, the intramolecular hydrogen bond is disrupted by polar solvents and the acetamido group adopts a position out of the plane of the aromatic ring. These changes are studied by means of changes in the deshielding effect of the amide carbonyl group on the remaining ortho proton.

Memory of chirality in rebound cyclizations of α-amide radicals

2013 ◽  
Vol 91 (1) ◽  
pp. 1-5 ◽  
Author(s):  
Aniruddha Sasmal ◽  
Tsuyoshi Taniguchi ◽  
Peter Wipf ◽  
Dennis P. Curran
Keyword(s):  
Carbonyl Group ◽  
Tert Butyl ◽  
Tributyltin Hydride ◽  
Memory Of Chirality ◽  
Amide Carbonyl ◽  
Amide Carbonyl Group

Reduction of (S)-N-(2-bromoallyl)-N-(tert-butyl)-2-methyl-3-phenylpropanamide with tributyltin hydride provides (3S,4S)-3-benzyl-1-(tert-butyl)-3,4-dimethylpyrrolidin-2-one with about 80% retention of chirality at the stereocenter adjacent to the amide carbonyl group. This memory of chirality is suggested to occur by transfer of chirality from a stereocenter to an axis, then from the axis back to a new stereocenter.

ChemInform Abstract: SELECTIVE REDUCTION OF THE AMIDE CARBONYL GROUP IN DIPEPTIDES BY BORANE

1976 ◽  
Vol 7 (30) ◽  
pp. no-no
Author(s):  
R. W. ROESKE ◽  
F. L. WEITL ◽  
K. U. PRASAD ◽  
R. M. THOMPSON
Keyword(s):  
Carbonyl Group ◽  
Selective Reduction ◽  
Amide Carbonyl ◽  
Amide Carbonyl Group

Selective reduction of the amide carbonyl group in dipeptides by borane

1976 ◽  
Vol 41 (7) ◽  
pp. 1260-1261 ◽  
Author(s):  
Roger W. Roeske ◽  
Frederick L. Weitl ◽  
Kari U. Prasad ◽  
Richard M. Thompson
Keyword(s):  
Carbonyl Group ◽  
Selective Reduction ◽  
Amide Carbonyl ◽  
Amide Carbonyl Group

scholarly journals Crystal structure ofN-(3-oxobutanoyl)-L-homoserine lactone

2016 ◽  
Vol 72 (2) ◽  
pp. 136-139 ◽  
Author(s):  
R.W. Newberry ◽  
R.T. Raines
Keyword(s):  
Oxygen Atom ◽  
Carbonyl Group ◽  
Homoserine Lactone ◽  
Ester Carbonyl ◽  
Compound C ◽  
Ester Carbonyl Group ◽  
Oxygen Donor ◽  
Protein Receptors ◽  
Amide Carbonyl ◽  
Amide Carbonyl Group

The structure and absolute configuration of the title compound, C8H11NO4, which is a known quorum-sensing modulator, have been determined. The molecule exhibits signs of an intramolecular attractive carbonyl–carbonyln→π*interaction between the amide and lactone ester groups, specifically – a short contact of 2.709 (2) Å between the amide oxygen atom and ester carbon atom, approach of the amide oxygen atom to the ester carbonyl group along the Bürgi–Dunitz trajectory, at 99.1 (1)°, and pyramidalization of the ester carbonyl group by 1.1 (1)°. Moreover, a similarn→π*interaction is observed for the amide carbonyl group approached by the ketone oxygen donor. These interactions apparently affect the conformation of the uncomplexed molecule, which adopts a different shape when bound to protein receptors. In the crystal, the molecules form translational chains along theaaxisviaN—H...O hydrogen bonds.

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