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Automated synthesis protocol of sequence-defined oligo-urethane-amides using thiolactone chemistry

Joshua Holloway (UGent) , Chiel Mertens (UGent) , Filip Du Prez (UGent) and Nezha Badi (UGent)
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Abstract
An automated, iterative protocol for the synthesis of multifunctional, sequence-defined oligo-urethane-amides using thiolactone chemistry is reported. Here, sequenced functionalization of the backbone is easily introduced using commercially available primary amines. The chemistry is carried out on solid phase using different supports for better optimization of the synthetic protocol and in order to demonstrate the versatility of the approach. This technique is very effective for iterative synthesis and solid-phase chemistry and enables the exploration of full automation of this approach using a robotic peptide synthesizer. As a result, this automated protocol allows for the synthesis of a sequence-defined nonamer of high purity.
Keywords
SCALABLE SYNTHESIS, ONE-POT, POLYMERS, MACROMOLECULES, INFORMATION, POWERFUL, STRATEGY, AMINE, TOOL, automated synthesis, sequence-controlled polymers, solid-phase, thiolactone

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Citation

Please use this url to cite or link to this publication:

Chicago
Holloway, Joshua, Chiel Mertens, Filip Du Prez, and Nezha Badi. 2019. “Automated Synthesis Protocol of Sequence-defined Oligo-urethane-amides Using Thiolactone Chemistry.” Macromolecular Rapid Communications 40 (1).
APA
Holloway, J., Mertens, C., Du Prez, F., & Badi, N. (2019). Automated synthesis protocol of sequence-defined oligo-urethane-amides using thiolactone chemistry. MACROMOLECULAR RAPID COMMUNICATIONS, 40(1).
Vancouver
1.
Holloway J, Mertens C, Du Prez F, Badi N. Automated synthesis protocol of sequence-defined oligo-urethane-amides using thiolactone chemistry. MACROMOLECULAR RAPID COMMUNICATIONS. 2019;40(1).
MLA
Holloway, Joshua et al. “Automated Synthesis Protocol of Sequence-defined Oligo-urethane-amides Using Thiolactone Chemistry.” MACROMOLECULAR RAPID COMMUNICATIONS 40.1 (2019): n. pag. Print.
@article{8605243,
  abstract     = {An automated, iterative protocol for the synthesis of multifunctional, sequence-defined oligo-urethane-amides using thiolactone chemistry is reported. Here, sequenced functionalization of the backbone is easily introduced using commercially available primary amines. The chemistry is carried out on solid phase using different supports for better optimization of the synthetic protocol and in order to demonstrate the versatility of the approach. This technique is very effective for iterative synthesis and solid-phase chemistry and enables the exploration of full automation of this approach using a robotic peptide synthesizer. As a result, this automated protocol allows for the synthesis of a sequence-defined nonamer of high purity.},
  articleno    = {1800685},
  author       = {Holloway, Joshua and Mertens, Chiel and Du Prez, Filip and Badi, Nezha},
  issn         = {1022-1336},
  journal      = {MACROMOLECULAR RAPID COMMUNICATIONS},
  keywords     = {SCALABLE SYNTHESIS,ONE-POT,POLYMERS,MACROMOLECULES,INFORMATION,POWERFUL,STRATEGY,AMINE,TOOL,automated synthesis,sequence-controlled polymers,solid-phase,thiolactone},
  language     = {eng},
  number       = {1},
  pages        = {7},
  title        = {Automated synthesis protocol of sequence-defined oligo-urethane-amides using thiolactone chemistry},
  url          = {http://dx.doi.org/10.1002/marc.201800685},
  volume       = {40},
  year         = {2019},
}

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