Abstract
Serlyticin-A is a secondary metabolite first isolated from a culture of Serratia ureilytica grown using squid pen as the sole carbon/nitrogen source. A previous study by Kuo et al. demonstrated that it has antioxidative and antiproliferative properties. However, the proposed chemical structure of serlyticin-A is likely incorrect based on the thermodynamic instability of its three contiguous heteroatom-heteroatom bonds. Here, we use quantum chemical calculations to predict 1H and 13C chemical shifts for serlyticin-A and demonstrate a discrepancy between the calculated and experimental chemical shifts. We then propose several reasonable alternative structures for serlyticin-A. Considering the known antioxidant and antiproliferative activity of hydroxamic acids as well as their stability and prevalence in natural products of bacterial origin, we believe that serlyticin-A is most likely 3-indolylacetohydroxamic acid (4). We provide our rationale for this assignment as well as experimental data for pure 3-indolylacetohydroxamic acid obtained via de novo synthesis. This study highlights the power of computational NMR shift prediction to revise chemical structures for natural products like serlyticin-A.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3464-3468 |
| Number of pages | 5 |
| Journal | Journal of Natural Products |
| Volume | 82 |
| Issue number | 12 |
| DOIs | |
| State | Published - Dec 27 2019 |
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ASJC Scopus subject areas
- Analytical Chemistry
- Molecular Medicine
- Pharmacology
- Pharmaceutical Science
- Drug Discovery
- Complementary and alternative medicine
- Organic Chemistry
Cite this
Reconsidering the Structure of Serlyticin-A. / Tsui, Ka Yi; Tombari, Robert J.; Olson, David E.; Tantillo, Dean J.
In: Journal of Natural Products, Vol. 82, No. 12, 27.12.2019, p. 3464-3468.Research output: Contribution to journal › Article
}
TY - JOUR
T1 - Reconsidering the Structure of Serlyticin-A
AU - Tsui, Ka Yi
AU - Tombari, Robert J.
AU - Olson, David E.
AU - Tantillo, Dean J.
PY - 2019/12/27
Y1 - 2019/12/27
N2 - Serlyticin-A is a secondary metabolite first isolated from a culture of Serratia ureilytica grown using squid pen as the sole carbon/nitrogen source. A previous study by Kuo et al. demonstrated that it has antioxidative and antiproliferative properties. However, the proposed chemical structure of serlyticin-A is likely incorrect based on the thermodynamic instability of its three contiguous heteroatom-heteroatom bonds. Here, we use quantum chemical calculations to predict 1H and 13C chemical shifts for serlyticin-A and demonstrate a discrepancy between the calculated and experimental chemical shifts. We then propose several reasonable alternative structures for serlyticin-A. Considering the known antioxidant and antiproliferative activity of hydroxamic acids as well as their stability and prevalence in natural products of bacterial origin, we believe that serlyticin-A is most likely 3-indolylacetohydroxamic acid (4). We provide our rationale for this assignment as well as experimental data for pure 3-indolylacetohydroxamic acid obtained via de novo synthesis. This study highlights the power of computational NMR shift prediction to revise chemical structures for natural products like serlyticin-A.
AB - Serlyticin-A is a secondary metabolite first isolated from a culture of Serratia ureilytica grown using squid pen as the sole carbon/nitrogen source. A previous study by Kuo et al. demonstrated that it has antioxidative and antiproliferative properties. However, the proposed chemical structure of serlyticin-A is likely incorrect based on the thermodynamic instability of its three contiguous heteroatom-heteroatom bonds. Here, we use quantum chemical calculations to predict 1H and 13C chemical shifts for serlyticin-A and demonstrate a discrepancy between the calculated and experimental chemical shifts. We then propose several reasonable alternative structures for serlyticin-A. Considering the known antioxidant and antiproliferative activity of hydroxamic acids as well as their stability and prevalence in natural products of bacterial origin, we believe that serlyticin-A is most likely 3-indolylacetohydroxamic acid (4). We provide our rationale for this assignment as well as experimental data for pure 3-indolylacetohydroxamic acid obtained via de novo synthesis. This study highlights the power of computational NMR shift prediction to revise chemical structures for natural products like serlyticin-A.
UR - http://www.scopus.com/inward/record.url?scp=85076970544&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85076970544&partnerID=8YFLogxK
U2 - 10.1021/acs.jnatprod.9b00859
DO - 10.1021/acs.jnatprod.9b00859
M3 - Article
C2 - 31840986
AN - SCOPUS:85076970544
VL - 82
SP - 3464
EP - 3468
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
IS - 12
ER -