An Advance in Proline Ligation

被引：93

作者：

Shang, Shiying ^{[1
]}

Tan, Zhongping ^{[1
]}

Dong, Suwei ^{[1
]}

Danishefsky, Samuel J. ^{[1
,2
]}

机构：

[1] Sloan Kettering Inst Canc Res, Bioorgan Chem Lab, New York, NY 10065 USA

[2] Columbia Univ, Dept Chem, New York, NY 10027 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 28期

关键词：

NATIVE CHEMICAL LIGATION; PROTEIN-SYNTHESIS; GLYCOPEPTIDE SYNTHESIS; THIYL RADICALS; PEPTIDE; CYSTEINE; DESULFURIZATION; RECOGNITION; EFFICIENT; INSIGHTS;

D O I：

10.1021/ja204277b

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Native chemical ligation (NCL) is widely applicable for building proteins in the laboratory. Since the discovery of this method, many strategies have been developed to enhance its capability and efficiency. Because of the poor reactivity of proline thioesters, ligation at a C-terminal proline site is not readily accomplished. Here, we demonstrate that ligation at an N-terminal protein is feasible using the combined logic of NCL and metal-free dethiylation (MFD).

引用

页码：10784 / 10786

页数：3

共 32 条

[21] Application of the logic of cysteine-free native chemical ligation to the synthesis of Human Parathyroid Hormone (hPTH) [J].

Shang, Shiying ;

Tan, Zhongping ;

Danishefsky, Samuel J. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2011, 108 (15) :5986-5989

[22] Peptide synthesis using unprotected peptides through orthogonal coupling methods [J].

Tam, JP ;

Lu, YA ;

Liu, CF ;

Shao, J .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1995, 92 (26) :12485-12489

[23] Rational development of a strategy for modifying the aggregatibility of proteins [J].

Tan, Zhongping ;

Shang, Shiying ;

Danishefsky, Samuel J. .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 2011, 108 (11) :4297-4302

[24] Insights into the Finer Issues of Native Chemical Ligation: An Approach to Cascade Ligations [J].

Tan, Zhongping ;

Shang, Shiying ;

Danishefsky, Samuel J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (49) :9500-9503

[25] Toward Homogeneous Erythropoietin: Non-NCL-Based Chemical Synthesis of the Gln78-Arg166 Glycopeptide Domain [J].

Tan, Zhongping ;

Shang, Shiying ;

Halkina, Tamara ;

Yuan, Yu ;

Danishefsky, Samuel J. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (15) :5424-5431

[26] PROLINE MOTIFS IN PEPTIDES AND THEIR BIOLOGICAL PROCESSING [J].

VANHOOF, G ;

GOOSSENS, F ;

DEMEESTER, I ;

HENDRIKS, D ;

SCHARPE, S .

FASEB JOURNAL, 1995, 9 (09) :736-744

[27] SOME EXTENSIONS OF THE REACTION OF TRIVALENT PHOSPHORUS DERIVATIVES WITH ALKOXY AND THIYL RADICALS - A NEW SYNTHESIS OF THIOESTERS [J].

WALLING, C ;

BASEDOW, OH ;

SAVAS, ES .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1960, 82 (09) :2181-2184

[28] THE REACTION OF THIYL RADICALS WITH TRIALKYL PHOSPHITES [J].

WALLING, C ;

RABINOWITZ, R .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1957, 79 (19) :5326-5326

[29] Free-radical-based, specific desulfurization of cysteine: A powerful advance in the synthesis of polypeptides and glycopolypeptides [J].

Wan, Qian ;

Danishefsky, Samuel J. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (48) :9248-9252

[30] Toward fully synthetic glycoproteins by ultimately convergent routes: A solution to a long-standing problem [J].

Warren, JD ;

Miller, JS ;

Keding, SJ ;

Danishefsky, SJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (21) :6576-6578

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