Thiophene Backbone Amide Linkers, a New Class of Easily Prepared and Highly Acid-Labile Linkers for Solid-Phase Synthesis†

2006 ◽  
Vol 71 (18) ◽  
pp. 6734-6741 ◽  
Author(s):  
Mikkel Jessing ◽  
Malene Brandt ◽  
Knud J. Jensen ◽  
Jørn B. Christensen ◽  
Ulrik Boas
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
New Class ◽  
Backbone Amide ◽  
Acid Labile

Backbone Amide Linker Strategies for the Solid-Phase Synthesis of C-Terminal Modified Peptides

ChemInform ◽  
2006 ◽  
Vol 37 (9) ◽  
Author(s):  
Jordi Alsina ◽  
Steven A. Kates ◽  
George Barany ◽  
Fernando Albericio
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Backbone Amide ◽  
Modified Peptides ◽  
Backbone Amide Linker

Solid Phase Synthesis of a Somatostatin Amide Analogue Using Acid Labile t-Bumeoc Protection and an Acid Labile Anchor Group

1992 ◽  
Vol 57 (8) ◽  
pp. 1707-1718
Author(s):  
Wolfgang Voelter ◽  
Gerhard Breipohl ◽  
Chryssa Tzougraki ◽  
Eveline Jungfleisch-Turgut
Keyword(s):  
Amino Acids ◽  
Acetic Acid ◽  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Somatostatin Analogue ◽  
Phase Synthesis ◽  
Anchor Group ◽  
Amide Form ◽  
Polystyrene Resin ◽  
Acid Labile

The solid phase synthesis of an amidated somatostatin analogue based on the principle of differentiated acidolysis is described. The acid labile and smoothly cleavable t-Bumeoc moiety (1% TFA/DCM) is used for temporary Nα-protection of D- and L-amino acids and [4-[[[9H-fluoren-9-yl-methoxycarbonyl]amino](4-methoxyphenyl)methyl]-2-methylphenoxy]acetic acid, attached to an aminomethylated polystyrene resin is used as acid sensitive linker of the solid carrier which releases the peptide in its amide form by treatment with TFA. Its preparation is described in detail.

Synthesis and applications of XAL, a new acid-labile handle for solid-phase synthesis of peptide amides

Peptides ◽  
1992 ◽  
pp. 601-602 ◽  
Author(s):  
Roger J. Bontems ◽  
Peter Hegyes ◽  
Susan L. Bontems ◽  
Fernando Albericio ◽  
George Barany
Keyword(s):  
Solid Phase Synthesis ◽  
Solid Phase ◽  
Phase Synthesis ◽  
Acid Labile
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