Chemical ligation from O-acyl isopeptides via 8-and 11-membered cyclic transition states

被引：4

作者：

Panda, Siva S. ^{[1
]}

Elagawany, Mohamed ^{[1
,2
]}

Marwani, Hadi M. ^{[3
]}

Caliskan, Eray ^{[1
]}

El Khatib, Mirna ^{[1
]}

Oliferenko, Alexander ^{[1
]}

Alamry, Khalid A. ^{[3
]}

Katritzky, Alan R. ^{[1
,3
]}

机构：

[1] Univ Florida, Dept Chem, Ctr Heterocycl Cpds, Gainesville, FL 32611 USA

[2] Misr Univ Sci & Technol, Coll Pharm, Dept Organ Chem, Al Motamayez Dist, Egypt

[3] King Abdulaziz Univ, Dept Chem, Jeddah 21589, Saudi Arabia

来源：

ARKIVOC | 2014年

关键词：

Ligation; serine; threonine; peptide; benzotriazole; NATIVE PEPTIDES; PHASE SYNTHESIS; STRATEGIES; BETA;

D O I：

10.3998/ark.5550190.p008.632

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Unprotected O-acylated serine and O-acylated threonine isopeptides have been synthesized, and their conversion to native tripeptides and tetrapeptides by O- to N-terminus transfer investigated. Ligations involving 8- and 11-membered cyclic transition states are shown experimentally and computationally to be more favorable than intermolecular cross-ligations.

引用

页码：91 / 106

页数：16

共 19 条

[1] Ligations from Tyrosine Isopeptides via 12-to 19-Membered Cyclic Transition States
Popov, Vadim
Panda, Siva S.
Katritzky, Alan R.
JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (15): : 7455 - 7461
[2] Ligations of O-acyl threonine units to give native peptides via 5-, 8-, 9-and 10-membered cyclic transition states
Panda, Siva S.
Liaqat, Sumaira
Tiwari, Anand D.
Marwani, Hadi M.
Faidallah, Hassan M.
Rauf, Abdul
Hall, C. Dennis
Katritzky, Alan R.
ARKIVOC, 2015, : 9 - 18
[3] Amide-forming chemical ligation via O-acyl hydroxamic acids
Dunkelmann, Daniel L.
Hirata, Yuki
Totaro, Kyle A.
Cohen, Daniel T.
Zhang, Chi
Gates, Zachary P.
Pentelute, Bradley L.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2018, 115 (15) : 3752 - 3757
[4] Synthesis of Unprotected Linear or Cyclic O-Acyl Isopeptides in Water Using Bis(2-sulfanylethyl)amido Peptide Ligation
Desmet, Remi
Pauzuolis, Mindaugas
Boll, Emmanuelle
Drobecq, Herve
Raibaut, Laurent
Melnyk, Oleg
ORGANIC LETTERS, 2015, 17 (13) : 3354 - 3357
[5] Traceless Chemical Ligation from S-, O-, and N-Acyl Isopeptides
Panda, Siva S.
Hall, C. Dennis
Oliferenko, Alexander A.
Katritzky, Alan R.
ACCOUNTS OF CHEMICAL RESEARCH, 2014, 47 (04) : 1076 - 1087
[6] SYNTHESIS OF UNPROTECTED LINEAR OR CYCLIC O-ACYL ISOPEPTIDES USING BIS(2-SULFANYLETHYL) AMIDO (SEA) PEPTIDE LIGATION AT ACIDIC PH
Melnyk, O.
Desmet, R.
Pauzuolis, M.
Boll, E.
Drobecq, H.
Raibaut, L.
JOURNAL OF PEPTIDE SCIENCE, 2016, 22 : S206 - S208
[7] Study of Chemical Ligation Via 17-, 18- and 19-Membered Cyclic Transition States
Panda, Siva S.
El-Nachef, Claudia
Bajaj, Kiran
Al-Youbi, Abdulrahman O.
Oliferenko, Alexander
Katritzky, Alan R.
CHEMICAL BIOLOGY & DRUG DESIGN, 2012, 80 (06) : 821 - 827
[8] Comparative properties of Aβ1-42, Aβ11-42, and [Pyr11] Aβ11-42 generated from O-acyl isopeptides
Sohma, Youhei
Yamasaki, Moe
Kawashima, Hiroyuki
Taniguchi, Atsuhiko
Yamashita, Masayuki
Akaji, Kenichi
Mukai, Hidehito
Kiso, Yoshiaki
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (05) : 1326 - 1329
[9] Chemical Ligation of S-Scylated Cysteine Peptides to Form Native Peptides via 5-, 11-, and 14-Membered Cyclic Transition States
Katritzky, Alan R.
Tala, Srinivasa R.
Abo-Dya, Nader E.
Ibrahim, Tarek S.
El-Feky, Said A.
Gyanda, Kapil
Pandya, Keyur M.
JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01): : 85 - 96
[10] S- to N-Acyl transfer in S-acylcysteine isopeptides via 9-, 10-, 12-, and 13-membered cyclic transition states
Bol'shakov, Oleg
Kovacs, Judit
Chahar, Mamta
Khanh Ha
Khelashvili, Levan
Katritzky, Alan R.
JOURNAL OF PEPTIDE SCIENCE, 2012, 18 (11) : 704 - 709

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