Alternating chemical ligation reactivity of S-acyl peptides explained with theory and computations

被引：16

作者：

Oliferenko, Alexander A. ^{[1
]}

Katritzky, Alan R. ^{[1
]}

机构：

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

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2011年 / 9卷 / 13期

关键词：

D O I：

10.1039/c1ob05536d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Previously discovered alternating reactivity of S-acyl di-, tri-, and tetrapeptide in internal chemical ligation reactions is rationalised using conformational search, virtual screening methods and quantum chemical calculations. Conformational preorganisation is shown to be the major controller of reactivity, with hydrogen bonding providing additional stabilisation for the tetrapeptide structure.

引用

页码：4756 / 4759

页数：4

共 10 条

[1]

ANELLI PL, 1985, J ORG CHEM, V50, P19

[2]

[Anonymous], PCMODEL V 9 2

[3] KINETICS OF ALKALINE HYDROLYSIS AND N-BUTYLAMINOLYSIS OF ETHYL P-NITROBENZOATE AND ETHYL P-NITROTHIOLBENZOATE [J].

CONNORS, KA ;

BENDER, ML .

JOURNAL OF ORGANIC CHEMISTRY, 1961, 26 (07) :2498-&

[4]

GRANOVSKY A, US GAMESS FIREFLY

[5]

Hibbert F., 1990, ADV PHYS ORG CHEM, V26, P255, DOI [DOI 10.1016/S0065-3160(08)60047-7, 10.1016/S0065-3160(08)60047-7]

[6] Chemical Ligation of S-Scylated Cysteine Peptides to Form Native Peptides via 5-, 11-, and 14-Membered Cyclic Transition States [J].

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

[7] The chemical ligation of selectively S-acylated cysteine peptides to form native peptides via 5-, 11-and 14-membered cyclic transition states [J].

Katritzky, Alan R. ;

Abo-Dya, Nader E. ;

Tala, Srinivasa R. ;

Abdel-Samii, Zakaria K. .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (10) :2316-2319

[8] Total chemical synthesis of proteins [J].

Kent, Stephen B. H. .

CHEMICAL SOCIETY REVIEWS, 2009, 38 (02) :338-351

[9] Hydrogen-bonding templated assemblies [J].

Vilar, R .

SUPRAMOLECULAR ASSEMBLY VIA HYDROGEN BONDS II, 2004, 111 :85-137

[10] Computational studies of the aminolysis of oxoesters and thioesters in aqueous solution [J].

Yang, W ;

Drueckhammer, DG .

ORGANIC LETTERS, 2000, 2 (26) :4133-4136

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