Solid-phase, solution, and segment condensation peptide syntheses incorporating chromium carbene complex-derived nonproteinogenic ("unnatural") amino acid fragments

1993 ◽  
Vol 115 (20) ◽  
pp. 9037-9047 ◽  
Author(s):  
Shon R. Pulley ◽  
Louis S. Hegedus
Keyword(s):  
Amino Acid ◽  
Solid Phase ◽  
Unnatural Amino Acid ◽  
Carbene Complex ◽  
Chromium Carbene ◽  
Segment Condensation ◽  
Phase Solution

scholarly journals Solid-Phase Synthesis of Callipeltin D. Stereochemical Confirmation of the Unnatural Amino Acid AGDHE

2005 ◽  
Vol 7 (26) ◽  
pp. 5881-5883 ◽  
Author(s):  
David C. Cranfill ◽  
Ángel I. Morales-Ramos ◽  
Mark A. Lipton
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Unnatural Amino Acid ◽  
Phase Synthesis

Epimerization During Coupling to the Unnatural Amino Acid in Solid Phase Peptide Synthesis

2001 ◽  
Vol 66 (6) ◽  
pp. 923-932 ◽  
Author(s):  
Zhenyu Zhang ◽  
Arthur Van Aerschot ◽  
Patrick Chaltin ◽  
Roger Busson ◽  
Piet Herdewijn
Keyword(s):  
Amino Acid ◽  
Nucleic Acids ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Unnatural Amino Acid ◽  
Side Chain

Extensive epimerization was observed during the coupling of Fmoc-L-Trp(Boc) and Fmoc-L-Pro to D-Ual, a synthetic α-amino acid with a nucleobase in the side chain. This unnatural amino acid was used extensively in the construction of nucleic acids recognition libraries. Reaction protocols based on the use of DIC-HOAt-DIEA mixture without preactivation of the coupling mixture has been proven to suppress the epimerization reaction significantly.

scholarly journals Semisynthetic protein nanoreactor for single-molecule chemistry

2015 ◽  
Vol 112 (45) ◽  
pp. 13768-13773 ◽  
Author(s):  
Joongoo Lee ◽  
Hagan Bayley
Keyword(s):  
Amino Acid ◽  
Single Molecule ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Ionic Current ◽  
Unnatural Amino Acid ◽  
Chemical Ligation ◽  
Single Molecule Level ◽  
Flow Through ◽  
Recombinant Polypeptides

The covalent chemistry of individual reactants bound within a protein pore can be monitored by observing the ionic current flow through the pore, which acts as a nanoreactor responding to bond-making and bond-breaking events. In the present work, we incorporated an unnatural amino acid into the α-hemolysin (αHL) pore by using solid-phase peptide synthesis to make the central segment of the polypeptide chain, which forms the transmembrane β-barrel of the assembled heptamer. The full-length αHL monomer was obtained by native chemical ligation of the central synthetic peptide to flanking recombinant polypeptides. αHL pores with one semisynthetic subunit were then used as nanoreactors for single-molecule chemistry. By introducing an amino acid with a terminal alkyne group, we were able to visualize click chemistry at the single-molecule level, which revealed a long-lived (4.5-s) reaction intermediate. Additional side chains might be introduced in a similar fashion, thereby greatly expanding the range of single-molecule covalent chemistry that can be investigated by the nanoreactor approach.

An Unnatural Amino Acid that Mimics a Tripeptide β-Strand and Forms β-Sheetlike Hydrogen-Bonded Dimers [J. Am. Chem. Soc.2000,122, 7654-7661]. 

2001 ◽  
Vol 123 (7) ◽  
pp. 1545-1546
Author(s):  
James S. Nowick ◽  
De Michael Chung ◽  
Kalyani Maitra ◽  
Santanu Maitra ◽  
Kimberly D. Stigers ◽  
...  
Keyword(s):  
Amino Acid ◽  
Unnatural Amino Acid ◽  
Hydrogen Bonded

A Strategy for Thioamide Incorporation During Fmoc Solid-Phase Peptide Synthesis with Robust Stereochemical Integrity

2019 ◽  
Author(s):  
luis camacho III ◽  
Bryan J. Lampkin ◽  
Brett VanVeller
Keyword(s):  
Amino Acid ◽  
Functional Groups ◽  
Peptide Synthesis ◽  
Solid Phase ◽  
Solid Phase Peptide Synthesis ◽  
Side Chains ◽  
Amino Acid Side Chains ◽  
Peptide Elongation

We describe a method to protect the sensitive stereochemistry of the thioamide—in analogy to the protection of the functional groups of amino acid side chains—in order to preserve the thioamide moiety during peptide elongation.<br>

A study of the MgCl2-tetrahydrofurane system

1985 ◽  
Vol 50 (11) ◽  
pp. 2422-2430 ◽  
Author(s):  
Karel Handlíř ◽  
Jaroslav Holeček ◽  
Ludvík Beneš
Keyword(s):  
Magnesium Chloride ◽  
Solid Phase ◽  
Saturated Solution ◽  
Solution Equilibrium ◽  
Tetragonal Crystals ◽  
Phase Solution

The solid phase-solution equilibrium has been studied in the MgCl2-tetrahydrofurane system. Below 28 °C the saturated solution of magnesium chloride is in equilibrium with the solid phase composed of MgCl2.4C4H8O, whereas at higher temperatures the equilibrium solvate has the composition of MgCl2.2C4H8O. The solvate MgCl2.4C4H8O forms tetragonal crystals composed of molecules of trans-dichloro-tetrakis(tetrahydrofurane)magnesium(II) complex. The solvate MgCl2.2C4H8O most probably represents a polymeric catena-di-μ-dichloro-trans-bis(tetrahydrofurane)magnesium(II) complex.

Oxytocin analogues with non-coded amino acid residues in position 8: [8-Neopentylglycine]oxytocin and [8-cycloleucine]oxytocin

1987 ◽  
Vol 52 (9) ◽  
pp. 2317-2325 ◽  
Author(s):  
Jan Hlaváček ◽  
Jan Pospíšek ◽  
Jiřina Slaninová ◽  
Walter Y. Chan ◽  
Victor J. Hruby
Keyword(s):  
Amino Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
The Other ◽  
Amino Acid Residues ◽  
Phase Synthesis ◽  
Other Hand ◽  
Fragment Condensation

[8-Neopentylglycine]oxytocin (II) and [8-cycloleucine]oxytocin (III) were prepared by a combination of solid-phase synthesis and fragment condensation. Both analogues exhibited decreased uterotonic potency in vitro, each being about 15-30% that of oxytocin. Analogue II also displayed similarly decreased uterotonic potency in vivo and galactogogic potency. On the other hand, analogue III exhibited almost the same potency as oxytocin in the uterotonic assay in vivo and in the galactogogic assay.

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