Peptide synthesis by fragment condensation on a soluble polymer support. 8. Maximum peptide chain lengths of carboxyl component peptides for effective coupling reactions with amino component peptides anchored to soluble and cross-linked polystyrene supports

The synthesis of histamine H2 receptors peptides was conducted using the methodology of solid phase assisted by microwaves. Microwaves can reduce the reaction times during the coupling and deprotection steps to obtain the desired peptide sequence. The coupling reaction was carried out with a mixture of N,N′-diisopropylcarbodiimide (DIC) and N,N,N′,N′-tetramethyl-O-(1H-benzotriazol-1-yl)uronium hexafluorophosphate (HBTU). The purity and yield are improved in peptide synthesis assisted by microwaves. Coupling reactions and deprotection on Rink resin were carried out in 5 min depending on amino acid and the length of the peptide chain.

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Pd-Catalyzed Functionalization of Aryl Amines on a Soluble Polymer Support

Synlett ◽

10.1055/s-0040-1707261 ◽

2020 ◽

Vol 31 (20) ◽

pp. 2027-2034

Author(s):

M. Manuel B. Marques ◽

A. Sofia Santos

Keyword(s):

Polymer Support ◽

Coupling Reactions ◽

Proof Of Concept ◽

Heck Reactions ◽

Soluble Polymer ◽

Cross Coupling Reactions ◽

Aryl Amines ◽

Catalyzed Reactions ◽

Metal Catalyzed ◽

Privileged Structures

AbstractHerein we report the use of a soluble polymer support PEG-2000 on Pd-catalyzed reactions to improve the functionalization of aromatic amines and the synthesis of N-heterocycles. Compatibility of metal-catalyzed reactions for assembling privileged structures such as functionalized anilines were studied. PEG-supported anilines were found to be suitable substrates for Pd-catalyzed N-arylation, Sonogashira and Heck reactions. PEGylated substrates were prepared in yields up to 94%. This work consists on a proof of concept on the use of PEGylated anilines on Pd-catalyzed cross-coupling reactions. Indole core was attained in 82% and 62% yields, via two different routes.

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Fmoc Solid Phase Peptide Synthesis

10.1093/oso/9780199637256.001.0001 ◽

1999 ◽

Cited By ~ 19

Keyword(s):

Peptide Synthesis ◽

Solid Phase ◽

Solid Phase Peptide Synthesis ◽

Peptide Chain ◽

Standard Approach ◽

Side Chain ◽

Complex Structures ◽

Protein Conjugation ◽

Chemoselective Ligation ◽

Routine Production

In the years since the publication of Atherton and Sheppard's volume, the technique of Fmoc solid-phase peptide synthesis has matured considerably and is now the standard approach for the routine production of peptides. The basic problems outstanding at the time of publication of this earlier work have now been, for the most part, solved. As a result, innovators in the field have focussed their efforts to develop methodologies and chemistry for the synthesis of more complex structures. The focus of this new volume is much broader, and covers not only the essential procedures for the production of linear peptides but also more advanced techniques for preparing cyclic, side-chain modified, phospho- and glycopeptides. Many other methods also deserving attention have been included: convergent peptide synthesis; peptide-protein conjugation; chemoselective ligation; and chemoselective purification. The difficult preparation of cysteine and methionine-containing peptides is also covered, as well as methods for overcoming aggregation during peptide chain assembly and a survey of available automated instrumentation.

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