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Shifting Native Chemical Ligation into Reverse through N→S Acyl Transfer.

Macmillan D, Adams A, Premdjee B - Isr. J. Chem. (2011)

Bottom Line: Reasons for this likely include the often straightforward method of precursor assembly using Fmoc-based chemistry and the fundamentally interesting acyl migration process.In this review we introduce recent advances in this exciting area and discuss, in more detail, our own efforts towards the synthesis of peptide thioesters through N→S acyl transfer in native peptide sequences.We have found that several peptide thioesters can be readily prepared and, what's more, there appears to be ample opportunity for further development and discovery.

View Article: PubMed Central - PubMed

Affiliation: Christopher Ingold Laboratories, Department of Chemistry, University College London 20 Gordon Street, London WC1H 0AJ, UK phone: +44 (0)20 7679 4684 e-mail: d.macmillan@ucl.ac.uk.

ABSTRACT
Peptide thioester synthesis by N→S acyl transfer is being intensively explored by many research groups the world over. Reasons for this likely include the often straightforward method of precursor assembly using Fmoc-based chemistry and the fundamentally interesting acyl migration process. In this review we introduce recent advances in this exciting area and discuss, in more detail, our own efforts towards the synthesis of peptide thioesters through N→S acyl transfer in native peptide sequences. We have found that several peptide thioesters can be readily prepared and, what's more, there appears to be ample opportunity for further development and discovery.

No MeSH data available.


Schematic thioester formation through N→S acyl shift, and some new routes to peptide thioesters using a) the cysteinyl proline ester (CPE) method;[10] b) N-alkyl cysteine;[9h, i] c) N-sulfanylethylanilides (SEAlide);[9f, 11] d) bis(2-sulfanylethyl)amide peptides (BSEA);[9c–e] e) N-methyl enamides, R3=linker.[9g] Species depicted in square brackets are not isolated.
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sch02: Schematic thioester formation through N→S acyl shift, and some new routes to peptide thioesters using a) the cysteinyl proline ester (CPE) method;[10] b) N-alkyl cysteine;[9h, i] c) N-sulfanylethylanilides (SEAlide);[9f, 11] d) bis(2-sulfanylethyl)amide peptides (BSEA);[9c–e] e) N-methyl enamides, R3=linker.[9g] Species depicted in square brackets are not isolated.


Shifting Native Chemical Ligation into Reverse through N→S Acyl Transfer.

Macmillan D, Adams A, Premdjee B - Isr. J. Chem. (2011)

Schematic thioester formation through N→S acyl shift, and some new routes to peptide thioesters using a) the cysteinyl proline ester (CPE) method;[10] b) N-alkyl cysteine;[9h, i] c) N-sulfanylethylanilides (SEAlide);[9f, 11] d) bis(2-sulfanylethyl)amide peptides (BSEA);[9c–e] e) N-methyl enamides, R3=linker.[9g] Species depicted in square brackets are not isolated.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3277902&req=5

sch02: Schematic thioester formation through N→S acyl shift, and some new routes to peptide thioesters using a) the cysteinyl proline ester (CPE) method;[10] b) N-alkyl cysteine;[9h, i] c) N-sulfanylethylanilides (SEAlide);[9f, 11] d) bis(2-sulfanylethyl)amide peptides (BSEA);[9c–e] e) N-methyl enamides, R3=linker.[9g] Species depicted in square brackets are not isolated.
Bottom Line: Reasons for this likely include the often straightforward method of precursor assembly using Fmoc-based chemistry and the fundamentally interesting acyl migration process.In this review we introduce recent advances in this exciting area and discuss, in more detail, our own efforts towards the synthesis of peptide thioesters through N→S acyl transfer in native peptide sequences.We have found that several peptide thioesters can be readily prepared and, what's more, there appears to be ample opportunity for further development and discovery.

View Article: PubMed Central - PubMed

Affiliation: Christopher Ingold Laboratories, Department of Chemistry, University College London 20 Gordon Street, London WC1H 0AJ, UK phone: +44 (0)20 7679 4684 e-mail: d.macmillan@ucl.ac.uk.

ABSTRACT
Peptide thioester synthesis by N→S acyl transfer is being intensively explored by many research groups the world over. Reasons for this likely include the often straightforward method of precursor assembly using Fmoc-based chemistry and the fundamentally interesting acyl migration process. In this review we introduce recent advances in this exciting area and discuss, in more detail, our own efforts towards the synthesis of peptide thioesters through N→S acyl transfer in native peptide sequences. We have found that several peptide thioesters can be readily prepared and, what's more, there appears to be ample opportunity for further development and discovery.

No MeSH data available.