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Solid-phase synthesis of peptides using allylic anchoring groups. An investigation of their palladium-catalysed cleavage

โœ Scribed by Paul Lloyd-Williams; Gemma Jou; Fernando Albericio; Ernest Giralt


Publisher
Elsevier Science
Year
1991
Tongue
French
Weight
363 KB
Volume
32
Category
Article
ISSN
0040-4039

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โœฆ Synopsis


The use of two dlfferent allylx "handles" has been mvcstlgated m the s&d-phase synthesis of protected peptldes Very iilgh ylcld3 for the cleavage ofpeptldes from the resin, under mdd condmons which preserve sidecham protcctmg groups can be achieved by caqmg out the cleavage reactmn m 2 2 1 THF/DMSO/O 5 M HCI,


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Solid-phase synthesis of peptides using
โœ Paul Lloyd-Williams; Ahmed Merzouk; Franรงois Guibรฉ; Fernando Albericio; Ernest G ๐Ÿ“‚ Article ๐Ÿ“… 1994 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 384 KB

High yklds for the cleavage reaction of Fmoc-protected peptide segments fmn an allylic handle may be obtained using tributyltin hydride in the jmsence of (ph3P)PdQ in a 1:l mixture of DMF/DCM. Altematively tbe cleavage reacdon may be carried out using NMA as nuclecpbile in a 2:2:1 mixture of DMSOfl'

Use of an allylic anchor group and of it
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protected The allylic handle -0-CH2-CH-CH-CH2-0-CH2-CO-has been used in the synthesis of peptide fro ments on aminomethyl polystyrene. The palladium-catalyzed hydrostannolytic cleavage il of t e peptide fragments from the resin occurs under very mild conditions.

Solid-phase synthesis of peptide nucleic
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A new simple solid-phase method has been developed for synthesizing Boc-protected peptide nucleic acid (PNA) monomers. An immobilized backbone 3 was built on Expansin ยฎ resin using an ester disulphide handle: 2-hydroxypropyl-dithio-2%-isobutyric acid (HPDI). The base acetic acids of thymine 5, Z-cyt