Abstract
A rapid, simplified and highly efficient continuous-flow solid-phase peptide synthesis technology is reported for the direct synthesis of mono and multiple N-methylated cyclic alanine and valine peptides. Through an optimization study, we find that only 1.5 equivalents of the amino acids are sufficient for the couplings to maintain excellent conversions. Importantly, the technology is outstandingly sustainable, since three chemical steps are cancelled from the procedure and low amount of solvent is used, compared to traditional technologies. Furthermore, it is also applicable to the coupling of challenging amino acids, since pentavalines were constructed with high yield. The technology was successfully upscaled and peptide cyclization was carried out too. [Figure not available: see fulltext.].
| Original language | English |
|---|---|
| Pages (from-to) | 21-27 |
| Number of pages | 7 |
| Journal | Journal of Flow Chemistry |
| Volume | 8 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - Mar 1 2018 |
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Keywords
- continuous-flow
- N-methylation
- peptides
- peptidomimetics
- SPPS
- synthesis
ASJC Scopus subject areas
- Chemistry (miscellaneous)
- Fluid Flow and Transfer Processes
- Organic Chemistry
Cite this
Sustainable synthesis of N-methylated peptides in a continuous-flow fixed bed reactor. / Szloszár, Aliz; Mándity, I.; Fülöp, F.
In: Journal of Flow Chemistry, Vol. 8, No. 1, 01.03.2018, p. 21-27.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Sustainable synthesis of N-methylated peptides in a continuous-flow fixed bed reactor
AU - Szloszár, Aliz
AU - Mándity, I.
AU - Fülöp, F.
PY - 2018/3/1
Y1 - 2018/3/1
N2 - A rapid, simplified and highly efficient continuous-flow solid-phase peptide synthesis technology is reported for the direct synthesis of mono and multiple N-methylated cyclic alanine and valine peptides. Through an optimization study, we find that only 1.5 equivalents of the amino acids are sufficient for the couplings to maintain excellent conversions. Importantly, the technology is outstandingly sustainable, since three chemical steps are cancelled from the procedure and low amount of solvent is used, compared to traditional technologies. Furthermore, it is also applicable to the coupling of challenging amino acids, since pentavalines were constructed with high yield. The technology was successfully upscaled and peptide cyclization was carried out too. [Figure not available: see fulltext.].
AB - A rapid, simplified and highly efficient continuous-flow solid-phase peptide synthesis technology is reported for the direct synthesis of mono and multiple N-methylated cyclic alanine and valine peptides. Through an optimization study, we find that only 1.5 equivalents of the amino acids are sufficient for the couplings to maintain excellent conversions. Importantly, the technology is outstandingly sustainable, since three chemical steps are cancelled from the procedure and low amount of solvent is used, compared to traditional technologies. Furthermore, it is also applicable to the coupling of challenging amino acids, since pentavalines were constructed with high yield. The technology was successfully upscaled and peptide cyclization was carried out too. [Figure not available: see fulltext.].
KW - continuous-flow
KW - N-methylation
KW - peptides
KW - peptidomimetics
KW - SPPS
KW - synthesis
UR - http://www.scopus.com/inward/record.url?scp=85045115524&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85045115524&partnerID=8YFLogxK
U2 - 10.1007/s41981-018-0002-9
DO - 10.1007/s41981-018-0002-9
M3 - Article
AN - SCOPUS:85045115524
VL - 8
SP - 21
EP - 27
JO - Journal of Flow Chemistry
JF - Journal of Flow Chemistry
SN - 2062-249X
IS - 1
ER -