Tandem deprotection-dimerization-macrocyclization route to C2 symmetric cyclo-tetrapeptides

Khanh Ha; Iryna Oleksandrivna Lebedyeva; Sadra Hamedzadeh; Zhiliang Li; Ryan Quiñones; Girinath G. Pillai; Byron Williams; Amir Nasajpour; Kristin Martin; Abdullah M. Asiri; Alan R. Katritzky

doi:10.1002/chem.201304262

Tandem deprotection-dimerization-macrocyclization route to C₂ symmetric cyclo-tetrapeptides

Khanh Ha, Iryna Oleksandrivna Lebedyeva, Sadra Hamedzadeh, Zhiliang Li, Ryan Quiñones, Girinath G. Pillai, Byron Williams, Amir Nasajpour, Kristin Martin, Abdullah M. Asiri, Alan R. Katritzky

Research output: Contribution to journal › Article › peer-review

5 Scopus citations

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	https://doi.org/10.1002/chem.201304262
State	Published - Apr 22 2014
Externally published	Yes

Keywords

benzotriazoles
cyclodimerization
lactamization
macrocycles
peptides

ASJC Scopus subject areas

Catalysis
Chemistry(all)
Organic Chemistry

Access to Document

10.1002/chem.201304262

Fingerprint Dive into the research topics of 'Tandem deprotection-dimerization-macrocyclization route to C<sub>2</sub> symmetric cyclo-tetrapeptides'. Together they form a unique fingerprint.

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 › peer-review

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. / Tandem deprotection-dimerization-macrocyclization route to C₂ symmetric cyclo-tetrapeptides. In: Chemistry - A European Journal. 2014 ; Vol. 20, No. 17. pp. 4874-4879.

@article{72bea108747045c3b035ebec3e618391,

title = "Tandem deprotection-dimerization-macrocyclization route to C2 symmetric cyclo-tetrapeptides",

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).",

keywords = "benzotriazoles, cyclodimerization, lactamization, macrocycles, peptides",

author = "Khanh Ha and Lebedyeva, {Iryna Oleksandrivna} and Sadra Hamedzadeh and Zhiliang Li and Ryan Qui{\~n}ones and Pillai, {Girinath G.} and Byron Williams and Amir Nasajpour and Kristin Martin and Asiri, {Abdullah M.} and Katritzky, {Alan R.}",

year = "2014",

month = apr,

day = "22",

doi = "10.1002/chem.201304262",

language = "English (US)",

volume = "20",

pages = "4874--4879",

journal = "Chemistry - A European Journal",

issn = "0947-6539",

publisher = "Wiley-VCH Verlag",

number = "17",

}

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 -