Synthesis and use of a pseudo-cysteine for native chemical ligation.
J Pept Sci
; 9(4): 221-8, 2003 Apr.
Article
de En
| MEDLINE
| ID: mdl-12725243
ABSTRACT
The process of native chemical ligation (NCL) is well described in the literature. An N-terminal cysteine-containing peptide reacts with a C-terminal thioester-containing peptide to yield a native amide bond after transesterification and acyl transfer. An N-terminal cysteine is required as both the N-terminal amino function and the sidechain thiol participate in the ligation reaction. In certain circumstances it is desirable, or even imperative, that the N-terminal region of a peptidic reaction partner remain unmodified, for Instance for the retention of biological activity after ligation. This work discusses the synthesis of a pseudo-N-terminal cysteine building block for incorporation into peptides using standard methods of solid phase synthesis. Upon deprotection, this building block affords a de facto N-terminal cysteine positioned on an amino acid sidechain. which is capable of undergoing native chemical ligation with a thioester. The syntheses of several peptides and structures containing this motif are detailed, their reactions discussed. and further applications of this technology proposed.
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Collection:
01-internacional
Base de données:
MEDLINE
Sujet principal:
Peptides
/
Cystéine
Langue:
En
Journal:
J Pept Sci
Sujet du journal:
BIOQUIMICA
Année:
2003
Type de document:
Article