The water molecule arrangement over the side chain of some aliphatic amino acids: A quantum chemical and bottom‐up investigation

2020 ◽  
Vol 120 (9) ◽  
Author(s):  
Giuseppe Lanza ◽  
Maria A. Chiacchio
Keyword(s):  
Amino Acids ◽  
Water Molecule ◽  
Quantum Chemical ◽  
Side Chain ◽  
Bottom Up

Water Molecules Hydrogen Bonding to Aromatic Acceptors of Amino Acids: the Structure of Tyr-Tyr-Phe Dihydrate and a Crystallographic Database Study on Peptides

1998 ◽  
Vol 54 (1) ◽  
pp. 25-31 ◽  
Author(s):  
Thomas Steiner ◽  
Antoine M. M. Schreurs ◽  
Jan A. Kanters ◽  
Jan Kroon
Keyword(s):  
Crystal Structure ◽  
Amino Acids ◽  
Hydrogen Bond ◽  
Hydrogen Bonding ◽  
Water Molecule ◽  
Side Chain ◽  
Protein Hydration ◽  
Water Molecules ◽  
Database Study ◽  
Wide Variability

The crystal structure of Tyr-Tyr-Phe dihydrate contains a hydrogen bond formed between a water molecule and the Phe side chain. The geometry is centered with a distance of 3.26 Å between the water O atom and the aromatic centroid. In a database study on hydrated peptides, four related examples are found which exhibit a wide variability of hydrogen-bond geometries. The intermolecular surroundings of the water molecules are inspected, showing that they are typically involved in complex networks of conventional and non-conventional hydrogen bonds. Possible relevance for protein hydration is given.

13C nuclear magnetic resonance study of cyclodipeptides containing 13C enriched hydrophobic amino acids

1980 ◽  
Vol 45 (2) ◽  
pp. 482-490 ◽  
Author(s):  
Jaroslav Vičar ◽  
François Piriou ◽  
Pierre Fromageot ◽  
Karel Bláha ◽  
Serge Fermandjian
Keyword(s):  
Amino Acids ◽  
Nuclear Magnetic Resonance ◽  
Nuclear Magnetic Resonance Study ◽  
Coupling Constants ◽  
Side Chain ◽  
Amino Acid Residues ◽  
Magnetic Resonance Study ◽  
Side Chain Conformation ◽  
13C Nuclear Magnetic Resonance ◽  
Hydrophobic Amino Acids

The diastereoisomeric pairs of cyclodipeptides cis- and trans-cyclo(Ala-Ala), cyclo(Ala-Phe), cyclo(Val-Val) and cyclo(Leu-Leu) containing 85% 13C enriched amino-acid residues were synthesized and their 13C-13C coupling constants were measured. The combination of 13C-13C and 1H-1H coupling constants enabled to estimate unequivocally the side chain conformation of the valine and leucine residues.

Peptide Modifications: Versatile Tools in Peptide and Natural Product Syntheses

Synlett ◽  
2019 ◽  
Vol 30 (11) ◽  
pp. 1289-1302 ◽  
Author(s):  
Phil Servatius ◽  
Lukas Junk ◽  
Uli Kazmaier
Keyword(s):  
Amino Acids ◽  
Natural Product ◽  
Bond Activation ◽  
Bond Formation ◽  
Side Chain ◽  
Peptide Backbone ◽  
Claisen Rearrangements ◽  
The Past ◽  
Allylic Alkylations ◽  
Peptide Modifications

Peptide modifications via C–C bond formation have emerged as valuable tools for the preparation and alteration of non-proteinogenic amino acids and the corresponding peptides. Modification of glycine subunits in peptides allows for the incorporation of unusual side chains, often in a highly stereoselective manner, orchestrated by the chiral peptide backbone. Moreover, modifications of peptides are not limited to the peptidic backbone. Many side-chain modifications, not only by variation of existing functional groups, but also by C–H functionalization, have been developed over the past decade. This account highlights the synthetic contributions made by our group and others to the field of peptide modifications and their application in natural product syntheses.1 Introduction2 Peptide Backbone Modifications via Peptide Enolates2.1 Chelate Enolate Claisen Rearrangements2.2 Allylic Alkylations2.3 Miscellaneous Modifications3 Side-Chain Modifications3.1 C–H Activation3.1.1 Functionalization via Csp3–H Bond Activation3.2.2 Functionalization via Csp2–H Bond Activation3.2 On Peptide Tryptophan Syntheses4 Conclusion

Enhanced hydrate formation by natural-like hydrophobic side chain amino acids at ambient temperature: A kinetics and morphology investigation

Fuel ◽  
2021 ◽  
Vol 299 ◽  
pp. 120828
Author(s):  
Kan Jeenmuang ◽  
Chakorn Viriyakul ◽  
Katipot Inkong ◽  
Hari Prakash Veluswamy ◽  
Santi Kulprathipanja ◽  
...  
Keyword(s):  
Amino Acids ◽  
Ambient Temperature ◽  
Hydrate Formation ◽  
Side Chain

Redesign of (R)-Omega-Transaminase and Its Application for Synthesizing Amino Acids with Bulky Side Chain

2021 ◽  
Author(s):  
Dong-Xu Jia ◽  
Chen Peng ◽  
Jun-Liang Li ◽  
Fan Wang ◽  
Zhi-Qiang Liu ◽  
...  
Keyword(s):  
Amino Acids ◽  
Side Chain ◽  
Bulky Side Chain

Vanadocene complexes of amino acids bearing functional group in the side chain

2013 ◽  
Vol 405 ◽  
pp. 121-127 ◽  
Author(s):  
Jaromír Vinklárek ◽  
Jan Honzíček ◽  
Milan Erben ◽  
Iva Klepalová ◽  
Aleš Eisner ◽  
...  
Keyword(s):  
Amino Acids ◽  
Functional Group ◽  
Side Chain

Synthesis of Alanine and Proline Amino Acids with Amino or Guanidinium Substitution on the Side Chain

Tetrahedron ◽  
2000 ◽  
Vol 56 (16) ◽  
pp. 2513-2522 ◽  
Author(s):  
Zhenyu Zhang ◽  
Arthur Van Aerschot ◽  
Chris Hendrix ◽  
Roger Busson ◽  
Frank David ◽  
...  
Keyword(s):  
Amino Acids ◽  
Side Chain
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