An Efficient One-Pot Four-Segment Condensation Method for Protein Chemical Synthesis

Successive peptide ligation using a one‐pot method can improve the efficiency of protein chemical synthesis. Although one‐pot three‐segment ligation has enjoyed widespread application, a robust method for one‐pot four‐segment ligation had to date remained undeveloped. Herein we report a new one‐pot...

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Published inAngewandte Chemie International Edition Vol. 54; no. 19; pp. 5713 - 5717
Main Authors Tang, Shan, Si, Yan-Yan, Wang, Zhi-Peng, Mei, Kun-Rong, Chen, Xin, Cheng, Jing-Yuan, Zheng, Ji-Shen, Liu, Lei
Format Journal Article
LanguageEnglish
Published Weinheim WILEY-VCH Verlag 04.05.2015
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Abstract Successive peptide ligation using a one‐pot method can improve the efficiency of protein chemical synthesis. Although one‐pot three‐segment ligation has enjoyed widespread application, a robust method for one‐pot four‐segment ligation had to date remained undeveloped. Herein we report a new one‐pot multisegment peptide ligation method that can be used to condense up to four segments with operational simplicity and high efficiency. Its practicality is demonstrated by the one‐pot four‐segment synthesis of a plant protein, crambin, and a human chemokine, hCCL21. Pick up a peptide: Tfacm‐protected cysteine is readily activated by pH adjustment, enabling the development of a highly efficient one‐pot four‐segment ligation method. Two proteins, crambin and the chemokine hCCL21, are prepared using this rapid and high‐yielding synthetic route.
AbstractList Successive peptide ligation using a one-pot method can improve the efficiency of protein chemical synthesis. Although one-pot three-segment ligation has enjoyed widespread application, a robust method for one-pot four-segment ligation had to date remained undeveloped. Herein we report a new one-pot multisegment peptide ligation method that can be used to condense up to four segments with operational simplicity and high efficiency. Its practicality is demonstrated by the one-pot four-segment synthesis of a plant protein, crambin, and a human chemokine, hCCL21.
Successive peptide ligation using a one-pot method can improve the efficiency of protein chemical synthesis. Although one-pot three-segment ligation has enjoyed widespread application, a robust method for one-pot four-segment ligation had to date remained undeveloped. Herein we report a new one-pot multisegment peptide ligation method that can be used to condense up to four segments with operational simplicity and high efficiency. Its practicality is demonstrated by the one-pot four-segment synthesis of a plant protein, crambin, and a human chemokine, hCCL21. Pick up a peptide: Tfacm-protected cysteine is readily activated by pH adjustment, enabling the development of a highly efficient one-pot four-segment ligation method. Two proteins, crambin and the chemokine hCCL21, are prepared using this rapid and high-yielding synthetic route.
Successive peptide ligation using a one‐pot method can improve the efficiency of protein chemical synthesis. Although one‐pot three‐segment ligation has enjoyed widespread application, a robust method for one‐pot four‐segment ligation had to date remained undeveloped. Herein we report a new one‐pot multisegment peptide ligation method that can be used to condense up to four segments with operational simplicity and high efficiency. Its practicality is demonstrated by the one‐pot four‐segment synthesis of a plant protein, crambin, and a human chemokine, hCCL21. Pick up a peptide: Tfacm‐protected cysteine is readily activated by pH adjustment, enabling the development of a highly efficient one‐pot four‐segment ligation method. Two proteins, crambin and the chemokine hCCL21, are prepared using this rapid and high‐yielding synthetic route.
Successive peptide ligation using a one-pot method can improve the efficiency of protein chemical synthesis. Although one-pot three-segment ligation has enjoyed widespread application, a robust method for one-pot four-segment ligation had to date remained undeveloped. Herein we report a new one-pot multisegment peptide ligation method that can be used to condense up to four segments with operational simplicity and high efficiency. Its practicality is demonstrated by the one-pot four-segment synthesis of a plant protein, crambin, and a human chemokine, hCCL21.Successive peptide ligation using a one-pot method can improve the efficiency of protein chemical synthesis. Although one-pot three-segment ligation has enjoyed widespread application, a robust method for one-pot four-segment ligation had to date remained undeveloped. Herein we report a new one-pot multisegment peptide ligation method that can be used to condense up to four segments with operational simplicity and high efficiency. Its practicality is demonstrated by the one-pot four-segment synthesis of a plant protein, crambin, and a human chemokine, hCCL21.
Author Chen, Xin
Tang, Shan
Mei, Kun-Rong
Si, Yan-Yan
Zheng, Ji-Shen
Wang, Zhi-Peng
Cheng, Jing-Yuan
Liu, Lei
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Issue 19
Keywords SITE
HYDRAZIDES
CCL21
PEPTIDE LIGATION-DESULFURIZATION
X-RAY-STRUCTURE
peptides
protein chemical synthesis
CRAMBIN
solid-phase synthesis
N-SULFANYLETHYLANILIDE PEPTIDE
STRATEGIES
protecting groups
CHEMOKINE
native chemical ligation
Language English
License http://onlinelibrary.wiley.com/termsAndConditions#vor
2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
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Notes Ministry of Science and Technology - No. 2012AA02A700
istex:F3E58475E90DCCA48C8935BDF8B149094CFA8254
National Basic Research Program of China - No. 2013CB932800
NSFC - No. 91313301; No. 21225207; No. 21402206
This study was supported by the "863" Program of the Ministry of Science and Technology (2012AA02A700), the National Basic Research Program of China (973 program, No. 2013CB932800), and the NSFC (Nos. 91313301, 21225207, and 21402206).
ArticleID:ANIE201500051
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This study was supported by the “863” Program of the Ministry of Science and Technology (2012AA02A700), the National Basic Research Program of China (973 program, No. 2013CB932800), and the NSFC (Nos. 91313301, 21225207, and 21402206).
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2012; 51
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e_1_2_2_2_3
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Bang, D. (000354193300036.6) 2006; 118
Bang, D (WOS:000238501500021) 2006; 45
Piontek, C. (000354193300036.26) 2009; 121
Pan, M (WOS:000335947900005) 2014; 50
Thompson, RE (WOS:000323829600026) 2013; 52
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Siman, P (WOS:000322126900037) 2013; 52
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Tan, Z. (000354193300036.33) 2010; 122
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Kent, SBH (WOS:000264374600003) 2009; 38
Bang, D (WOS:000188834900033) 2004; 126
Raibaut, L (WOS:000309544700010) 2012; 41
Thompson, R. E. (000354193300036.36) 2013; 125
Piontek, C. (000354193300036.25) 2009; 48
Hackenberger, C. P. R. (000354193300036.15) 2008; 120
Bang, D (WOS:000221307600015) 2004; 43
Baumann, L. (000354193300036.7) 2013; 125
Baumann, L (WOS:000323474600029) 2013; 52
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– reference: D. Bang, V. Tereshko, A. A. Kossiakoff, S. B. H. Kent, Mol. BioSyst. 2009, 5, 750-756.
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Snippet Successive peptide ligation using a one‐pot method can improve the efficiency of protein chemical synthesis. Although one‐pot three‐segment ligation has...
Successive peptide ligation using a one-pot method can improve the efficiency of protein chemical synthesis. Although one-pot three-segment ligation has...
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StartPage 5713
SubjectTerms Activated
Adjustment
Chemical synthesis
Chemistry
Chemistry, Multidisciplinary
Chemokine CCL21 - chemical synthesis
Chemokine CCL21 - chemistry
Condensation
Condensing
Cysteine
Human
Humans
native chemical ligation
Peptides
Peptides - chemistry
Physical Sciences
Plant Proteins - chemical synthesis
Plant Proteins - chemistry
protecting groups
protein chemical synthesis
Proteins
Science & Technology
Segments
solid-phase synthesis
Synthesis
Title An Efficient One-Pot Four-Segment Condensation Method for Protein Chemical Synthesis
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