Abstract
A new method for the synthesis of cystathionine containing cyclic peptides has been developed. Conventionally such systems are typically made with relatively late-stage on-resin cyclisation involving reaction between a chlorohomoalanine and cysteine residue. We offer a different approach involving early incorporation of a cystathionine residue through on-resin reaction between a cysteine residue and an N-Alloc iodohomoalanine cumyl ester. Subsequent cyclisation then involves amide bond formation. The success of this method was demonstrated by applying it to the synthesis of a cystathionine analogue of the disulfide bridge cyclic peptide, N-acetylated cyclic peptide c[CVDINNNC]-NH2, a biologically active iNOS binding epitope mimetic that binds tightly to the protein, SPSB2. Our method expands the repertoire of synthetic options towards the construction of cystathionine containing cyclic peptides.
| Original language | English |
|---|---|
| Pages (from-to) | 3256-3261 |
| Number of pages | 6 |
| Journal | Tetrahedron |
| Volume | 72 |
| Issue number | 23 |
| DOIs | |
| Publication status | Published - 9 Jun 2016 |
Keywords
- Cyclopeptides
- Cystathionine
- SPSB2-iNOS
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An alternative approach to the synthesis of peptides containing a cystathionine bridge. / Harjani, Jitendra R.; Yap, Beow Keat; Norton, Raymond S.; Baell, Jonathan B.
In: Tetrahedron, Vol. 72, No. 23, 09.06.2016, p. 3256-3261.Research output: Contribution to journal › Article › Research › peer-review
TY - JOUR
T1 - An alternative approach to the synthesis of peptides containing a cystathionine bridge
AU - Harjani, Jitendra R.
AU - Yap, Beow Keat
AU - Norton, Raymond S.
AU - Baell, Jonathan B.
PY - 2016/6/9
Y1 - 2016/6/9
N2 - A new method for the synthesis of cystathionine containing cyclic peptides has been developed. Conventionally such systems are typically made with relatively late-stage on-resin cyclisation involving reaction between a chlorohomoalanine and cysteine residue. We offer a different approach involving early incorporation of a cystathionine residue through on-resin reaction between a cysteine residue and an N-Alloc iodohomoalanine cumyl ester. Subsequent cyclisation then involves amide bond formation. The success of this method was demonstrated by applying it to the synthesis of a cystathionine analogue of the disulfide bridge cyclic peptide, N-acetylated cyclic peptide c[CVDINNNC]-NH2, a biologically active iNOS binding epitope mimetic that binds tightly to the protein, SPSB2. Our method expands the repertoire of synthetic options towards the construction of cystathionine containing cyclic peptides.
AB - A new method for the synthesis of cystathionine containing cyclic peptides has been developed. Conventionally such systems are typically made with relatively late-stage on-resin cyclisation involving reaction between a chlorohomoalanine and cysteine residue. We offer a different approach involving early incorporation of a cystathionine residue through on-resin reaction between a cysteine residue and an N-Alloc iodohomoalanine cumyl ester. Subsequent cyclisation then involves amide bond formation. The success of this method was demonstrated by applying it to the synthesis of a cystathionine analogue of the disulfide bridge cyclic peptide, N-acetylated cyclic peptide c[CVDINNNC]-NH2, a biologically active iNOS binding epitope mimetic that binds tightly to the protein, SPSB2. Our method expands the repertoire of synthetic options towards the construction of cystathionine containing cyclic peptides.
KW - Cyclopeptides
KW - Cystathionine
KW - SPSB2-iNOS
UR - http://www.scopus.com/inward/record.url?scp=84965047851&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2016.04.051
DO - 10.1016/j.tet.2016.04.051
M3 - Article
VL - 72
SP - 3256
EP - 3261
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 23
ER -