A Solid-Phase Synthetic Route to Unnatural Amino Acids with Diverse Side-Chain Substitutions

2002 ◽  
Vol 67 (9) ◽  
pp. 2960-2969 ◽  
Author(s):  
William L. Scott ◽  
Martin J. O'Donnell ◽  
Francisca Delgado ◽  
Jordi Alsina
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Solid Phase ◽  
Side Chain ◽  
Synthetic Route

Solid-phase synthesis and utilization of side-chain reactive unnatural amino acids

2003 ◽  
Vol 44 (46) ◽  
pp. 8403-8406 ◽  
Author(s):  
Martin J. O'Donnell ◽  
Jordi Alsina ◽  
William L. Scott
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Side Chain ◽  
Phase Synthesis

The solid phase synthesis of α,α-disubstituted unnatural amino acids and peptides (di-UPS)

1997 ◽  
Vol 38 (21) ◽  
pp. 3695-3698 ◽  
Author(s):  
William L. Scott ◽  
Changyou Zhou ◽  
Zhiqiang Fang ◽  
Martin J. O'Donnell
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis

UPS on Weinreb Resin:  A Facile Solid-Phase Route to Aldehyde and Ketone Derivatives of “Unnatural” Amino Acids and Peptides

2000 ◽  
Vol 2 (2) ◽  
pp. 172-181 ◽  
Author(s):  
Martin J. O'Donnell ◽  
Mark D. Drew ◽  
Richard S. Pottorf ◽  
William L. Scott
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Solid Phase ◽  
Derivatives Of

Synthesis and Solid-Phase Applications of N-Tetrachlorophthaloyl (TCP) Side-Chain-Protected Amino Acids

Synlett ◽  
2006 ◽  
Vol 2006 (17) ◽  
pp. 2743-2746
Author(s):  
Eduard Bardají ◽  
Sylvie Monroc ◽  
Lidia Feliu ◽  
Judit Serra ◽  
Marta Planas
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Side Chain

A New and Efficient Synthesis of Unnatural Amino Acids and Peptides by Selective 3,3-Dimethyldioxirane Side-Chain Oxidation

1999 ◽  
Vol 64 (23) ◽  
pp. 8468-8474 ◽  
Author(s):  
Raffaele Saladino ◽  
Maurizio Mezzetti ◽  
Enrico Mincione ◽  
Ines Torrini ◽  
Mario Paglialunga Paradisi ◽  
...  
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Side Chain ◽  
Efficient Synthesis ◽  
Chain Oxidation

scholarly journals Oxytocin analogues with amide groups substituted by tetrazole groups in position 4, 5 or 9.

2007 ◽  
Vol 54 (4) ◽  
pp. 805-811 ◽  
Author(s):  
Michał Manturewicz ◽  
Zbigniew Grzonka ◽  
Lenka Borovicková ◽  
Jirina Slaninová
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Biological Activities ◽  
Synthesis Method ◽  
Oxytocin Receptor ◽  
Amide Group ◽  
Biologically Active ◽  
Side Chain ◽  
Electronic Effects

Eleven oxytocin analogues substituted in position 4, 5 or 9 by tetrazole analogues of amino acids were prepared using solid-phase peptide synthesis method and tested for rat uterotonic in vitro and pressor activities, as well as for their affinity to human oxytocin receptor. The tetrazolic group has been used as a bioisosteric substitution of carboxylic, ester or amide groups in structure-activity relationship studies of biologically active compounds. Replacement of the amide groups of Gln(4) and Asn(5) in oxytocin by tetrazole analogues of aspartic, glutamic and alpha-aminoadipic acids containing the tetrazole moiety in the side chains leads to analogues with decreased biological activities. Oxytocin analogues in which the glycine amide residue in position 9 was substituted by tetrazole analogues of glycine had diminished activities as well. The analysis of differences in rat uterotonic activity and in the affinity to human oxytocin receptors of analogues containing either an acidic 5-substituted tetrazolic group or a neutral 1,5- or 2,5-tetrazole nucleus makes it possible to draw some new conclusions concerning the role of the amide group of amino acids in positions 4, 5 and 9 of oxytocin for its activity. The data suggest that the interaction of the side chain of Gln(4) with the oxytocin receptor is influenced mainly by electronic effects and the hydrogen bonding capacity of the amide group. Steric effects of the side chain are minor. Substitution of Asn(5) by its tetrazole derivative gave an analogue of very low activity. The result suggests that in the interaction between the amide group of Asn(5) and the binding sites of oxytocic receptor hydrogen bonds are of less importance than the spatial requirements for this group.

Solid-phase synthesis of unnatural amino acids using unactivated alkyl halides

1997 ◽  
Vol 38 (41) ◽  
pp. 7163-7166 ◽  
Author(s):  
Martin J. O'Donnell ◽  
Charles W. Lugar ◽  
Richard S. Pottorf ◽  
Changyou Zhou ◽  
William L. Scott ◽  
...  
Keyword(s):  
Amino Acids ◽  
Unnatural Amino Acids ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Alkyl Halides ◽  
Phase Synthesis

Synthese eines Thymosin β10-Fragments zur Entwicklung spezifischer Antikörper / Synthesis of a Fragment of Thymosin β10 for the Development of Specific Antibodies

1992 ◽  
Vol 47 (8) ◽  
pp. 1170-1174 ◽  
Author(s):  
Susanne Hörger ◽  
Brigitte Gallert ◽  
Hartmut Echner ◽  
Wolfgang Voelter
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Protecting Groups ◽  
Side Chain ◽  
Phase Method ◽  
Preparative Hplc ◽  
Specific Antibodies ◽  
Tert Butyl ◽  
Thymosin Β10 ◽  
Solid Phase Method

The N-terminal fragment 1-12 of thymosin β10 was synthesized by the solid phase method using p-benzyloxybenzyl alcohol/polystyrene/divinylbenzeneresin and N-a-Fmoc amino acids with tert-butyl or Boc side chain protecting groups. Coupling was performed with BOP. The peptide was purified by preparative HPLC.

ChemInform Abstract: Solid-Phase N-Glycopeptide Synthesis Using Allyl Side-Chain Protected Fmoc-Amino Acids.

ChemInform ◽  
2010 ◽  
Vol 25 (26) ◽  
pp. no-no
Author(s):  
S. A. KATES ◽  
B. G. DE LA TORRE ◽  
R. ERITJA ◽  
F. ALBERICIO
Keyword(s):  
Amino Acids ◽  
Solid Phase ◽  
Side Chain
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