Abstract
Dimerization-macrocyclization has been a long-standing problem in the cyclization of peptides since, together with the desired cyclic product, many cyclic oligomers and linear polymers may also be formed during the reaction. Therefore, the development of a process that affords the cyclic dimer predominantly is difficult. A novel and versatile strategy for the synthesis of symmetric cyclo-tetrapeptides by palladium-promoted tandem deprotection/cyclo- dimerization from readily available Cbz-dipeptidoyl benzotriazolides is reported (Cbz=carboxybenzyl).
| Original language | English (US) |
|---|---|
| Pages (from-to) | 4874-4879 |
| Number of pages | 6 |
| Journal | Chemistry - A European Journal |
| Volume | 20 |
| Issue number | 17 |
| DOIs | |
| State | Published - Apr 22 2014 |
| Externally published | Yes |
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Keywords
- benzotriazoles
- cyclodimerization
- lactamization
- macrocycles
- peptides
ASJC Scopus subject areas
- Catalysis
- Chemistry(all)
- Organic Chemistry
Cite this
Tandem deprotection-dimerization-macrocyclization route to C2 symmetric cyclo-tetrapeptides. / Ha, Khanh; Lebedyeva, Iryna Oleksandrivna; Hamedzadeh, Sadra; Li, Zhiliang; Quiñones, Ryan; Pillai, Girinath G.; Williams, Byron; Nasajpour, Amir; Martin, Kristin; Asiri, Abdullah M.; Katritzky, Alan R.
In: Chemistry - A European Journal, Vol. 20, No. 17, 22.04.2014, p. 4874-4879.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Tandem deprotection-dimerization-macrocyclization route to C2 symmetric cyclo-tetrapeptides
AU - Ha, Khanh
AU - Lebedyeva, Iryna Oleksandrivna
AU - Hamedzadeh, Sadra
AU - Li, Zhiliang
AU - Quiñones, Ryan
AU - Pillai, Girinath G.
AU - Williams, Byron
AU - Nasajpour, Amir
AU - Martin, Kristin
AU - Asiri, Abdullah M.
AU - Katritzky, Alan R.
PY - 2014/4/22
Y1 - 2014/4/22
N2 - Dimerization-macrocyclization has been a long-standing problem in the cyclization of peptides since, together with the desired cyclic product, many cyclic oligomers and linear polymers may also be formed during the reaction. Therefore, the development of a process that affords the cyclic dimer predominantly is difficult. A novel and versatile strategy for the synthesis of symmetric cyclo-tetrapeptides by palladium-promoted tandem deprotection/cyclo- dimerization from readily available Cbz-dipeptidoyl benzotriazolides is reported (Cbz=carboxybenzyl).
AB - Dimerization-macrocyclization has been a long-standing problem in the cyclization of peptides since, together with the desired cyclic product, many cyclic oligomers and linear polymers may also be formed during the reaction. Therefore, the development of a process that affords the cyclic dimer predominantly is difficult. A novel and versatile strategy for the synthesis of symmetric cyclo-tetrapeptides by palladium-promoted tandem deprotection/cyclo- dimerization from readily available Cbz-dipeptidoyl benzotriazolides is reported (Cbz=carboxybenzyl).
KW - benzotriazoles
KW - cyclodimerization
KW - lactamization
KW - macrocycles
KW - peptides
UR - http://www.scopus.com/inward/record.url?scp=84899426457&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84899426457&partnerID=8YFLogxK
U2 - 10.1002/chem.201304262
DO - 10.1002/chem.201304262
M3 - Article
C2 - 24700372
AN - SCOPUS:84899426457
VL - 20
SP - 4874
EP - 4879
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 17
ER -