Convergent Synthesis of Thioether Containing Peptides

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Spyridon MourtasK Barlos

Abstract

Thioether containing peptides were obtained following three synthetic routes. In route A, halo acids esterified on 2-chlorotrityl(Cltr) resin were reacted with N-fluorenylmethoxycarbonyl (Fmoc) aminothiols. These were either cleaved from the resin to the corresponding (Fmoc-aminothiol)carboxylic acids, which were used as key building blocks in solid phase peptide synthesis (SPPS), or the N-Fmoc group was deprotected and peptide chains were elongated by standard SPPS. The obtained N-Fmoc protected thioether containing peptides were then condensed either in solution, or on solid support, with the appropriate amino components of peptides. In route B, the thioether containing peptides were obtained by the reaction of N-Fmoc aminothiols with bromoacetylated peptides, which were synthesized on Cltr-resin, followed by removal of the N-Fmoc group and subsequent peptide elongation by standard SPPS. In route C, the thioether containing peptides were obtained by the condensation of a haloacylated peptide synthesized on Cltr-resin and a thiol-peptide synthesized either on 4-methoxytrityl(Mmt) or trityl(Trt) resin.

References

May 28, 1979·Biochemical and Biophysical Research Communications·R H Marks, R D Miller
Jan 1, 1979·International Journal of Peptide and Protein Research·D HudsonM Szelke
Mar 1, 1988·Journal of Medicinal Chemistry·R E TenBrinkG A Johnson
Jan 1, 1997·Methods in Enzymology·Fernando AlbericioE Giralt
Mar 16, 2000·Journal of Peptide Science : an Official Publication of the European Peptide Society·Y NishiuchiT Kimura
May 15, 2001·The Journal of Peptide Research : Official Journal of the American Peptide Society·J MaríkJ Hlaváček
Oct 9, 2002·Mini Reviews in Medicinal Chemistry·Jung-Mo AhnKim D Janda
Sep 2, 2006·Molecular Biotechnology·Muriel AmblardGilles Subra
Nov 3, 2009·Drug Discovery Today·Patrick VliegheMichel Khrestchatisky
Aug 2, 2012·Current Protocols in Protein Science·Maciej Stawikowski, Gregg B Fields
Apr 12, 2013·ACS Combinatorial Science·Miriam Góngora-BenítezFernando Albericio
Mar 15, 2014·Chemical Society Reviews·Ilker AvanAlan R Katritzky
Jan 6, 2015·Methods in Molecular Biology·Pasqualina Liana ScognamiglioDaniela Marasco
Jan 21, 2016·Journal of Peptide Science : an Official Publication of the European Peptide Society·Raymond BehrendtJohn Offer
Nov 20, 2016·Drug Discovery Today·Nir QvitEric R Gross

Related Concepts

Composite Resins
Peptides
2-chlorotrityl chloride
Cleaved
N-(9H-(fluoren-9-ylmethoxy)carbonyl)glycine
Finding
Fatty Acids, Esterified
Route
Tpt1 protein, mouse
9-fluorenylmethoxycarbonyl

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Systemic Juvenile Idiopathic Arthritis

Systemic juvenile idiopathic arthritis is a rare rheumatic disease that affects children. Symptoms include joint pain, but also fevers and skin rashes. Here is the latest on this disease.

Chromatin Regulation and Circadian Clocks

The circadian clock plays an important role in regulating transcriptional dynamics through changes in chromatin folding and remodelling. Discover the latest research on Chromatin Regulation and Circadian Clocks here.

Central Pontine Myelinolysis

Central Pontine Myelinolysis is a neurologic disorder caused most frequently by rapid correction of hyponatremia and is characterized by demyelination that affects the central portion of the base of the pons. Here is the latest research on this disease.

Myocardial Stunning

Myocardial stunning is a mechanical dysfunction that persists after reperfusion of previously ischemic tissue in the absence of irreversible damage including myocardial necrosis. Here is the latest research.

Pontocerebellar Hypoplasia

Pontocerebellar hypoplasias are a group of neurodegenerative autosomal recessive disorders with prenatal onset, atrophy or hypoplasia of the cerebellum, hypoplasia of the ventral pons, microcephaly, variable neocortical atrophy and severe mental and motor impairments. Here is the latest research on pontocerebellar hypoplasia.

Cell Atlas Along the Gut-Brain Axis

Profiling cells along the gut-brain axis at the single cell level will provide unique information for each cell type, a three-dimensional map of how cell types work together to form tissues, and insights into how changes in the map underlie health and disease of the GI system and its crosstalk with the brain. Disocver the latest research on single cell analysis of the gut-brain axis here.

Chronic Traumatic Encephalopathy

Chronic Traumatic Encephalopathy (CTE) is a progressive degenerative disease that occurs in individuals that suffer repetitive brain trauma. Discover the latest research on traumatic encephalopathy here.