TY - JOUR
T1 - Natural dolapyrrolidone
T2 - Isolation and absolute stereochemistry of a substructure of bioactive peptides
AU - Murakami, Ayana
AU - Hayashi, Jun ichi
AU - Igawa, Kazunobu
AU - Tsutsumi, Miki
AU - Tomooka, Katsuhiko
AU - Nagai, Hiroshi
AU - Nehira, Tatsuo
N1 - Funding Information:
This research was supported by JSPS Grand‐in‐Aid for Scientific Research Grant Number 16K05696 to T. N. This work was also performed under the cooperative research program of “Network Joint Research Center for Materials and Devices” No. 20181281 to K. I. and T. N.
Funding Information:
This research was supported by JSPS Grand-in-Aid for Scientific Research Grant Number 16K05696 to T. N. This work was also performed under the cooperative research program of ?Network Joint Research Center for Materials and Devices? No. 20181281 to K. I. and T. N.
Publisher Copyright:
© 2020 Wiley Periodicals LLC.
PY - 2020/9/1
Y1 - 2020/9/1
N2 - During the course of our chemical analysis of the hydrophilic fractions from marine cyanobacterium Moorena producens, we have isolated natural dolapyrrolidone (Dpy, 1), a natural pyrrolidone derived from phenylalanine, for the first time as a single compound. Compound 1, with an (S)-l absolute stereochemistry, was previously identified as a substructure that is common among several bioactive natural peptides. Surprisingly, the absolute stereochemistry of the isolated natural 1, determined through total synthesis, was (R)-d. This result was unambiguously determined by HPLC analysis using a chiral stationary column by comparing the retention times of the natural 1 and authentic samples of synthetic enantiomers. To verify the unexpected result, the absolute stereochemistry of the natural 1 was confirmed by X-ray crystallographic analysis of Pt-complex derivative using the synthetic enantiomer.
AB - During the course of our chemical analysis of the hydrophilic fractions from marine cyanobacterium Moorena producens, we have isolated natural dolapyrrolidone (Dpy, 1), a natural pyrrolidone derived from phenylalanine, for the first time as a single compound. Compound 1, with an (S)-l absolute stereochemistry, was previously identified as a substructure that is common among several bioactive natural peptides. Surprisingly, the absolute stereochemistry of the isolated natural 1, determined through total synthesis, was (R)-d. This result was unambiguously determined by HPLC analysis using a chiral stationary column by comparing the retention times of the natural 1 and authentic samples of synthetic enantiomers. To verify the unexpected result, the absolute stereochemistry of the natural 1 was confirmed by X-ray crystallographic analysis of Pt-complex derivative using the synthetic enantiomer.
UR - http://www.scopus.com/inward/record.url?scp=85087177414&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85087177414&partnerID=8YFLogxK
U2 - 10.1002/chir.23264
DO - 10.1002/chir.23264
M3 - Article
C2 - 32602569
AN - SCOPUS:85087177414
SN - 0899-0042
VL - 32
SP - 1152
EP - 1159
JO - Chirality
JF - Chirality
IS - 9
ER -
