scholarly journals Total synthesis and biological activity of dolastatin 16

2017 ◽  
Vol 15 (5) ◽  
pp. 1140-1150 ◽  
Author(s):  
Loida O. Casalme ◽  
Arisa Yamauchi ◽  
Akinori Sato ◽  
Julie G. Petitbois ◽  
Yasuyuki Nogata ◽  
...  
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Sea Hare ◽  
Dolabella Auricularia

The total synthesis of dolastatin 16, a macrocyclic depsipeptide first isolated from the sea hareDolabella auriculariaas a potential antineoplastic metabolite by Pettitet al., was achieved in a convergent manner.

Total Synthesis of Doliculide, a Potent Cytotoxic Cyclodepsipeptide from the Japanese Sea Hare Dolabella auricularia

1994 ◽  
Vol 59 (17) ◽  
pp. 4712-4713 ◽  
Author(s):  
Hiroyuki Ishiwata ◽  
Hiroki Sone ◽  
Hideo Kigoshi ◽  
Kiyoyuki Yamada
Keyword(s):  
Total Synthesis ◽  
Sea Hare ◽  
Dolabella Auricularia

Aurilide, a cytotoxic depsipeptide from the sea hare Dolabella auricularia: isolation, structure determination, synthesis, and biological activity

Tetrahedron ◽  
2004 ◽  
Vol 60 (38) ◽  
pp. 8509-8527 ◽  
Author(s):  
Kiyotake Suenaga ◽  
Tsuyoshi Mutou ◽  
Takunobu Shibata ◽  
Takashi Itoh ◽  
Tatsuya Fujita ◽  
...  
Keyword(s):  
Biological Activity ◽  
Structure Determination ◽  
Sea Hare ◽  
Dolabella Auricularia

Recent advances in hapalindole-type cyanobacterial alkaloids: biosynthesis, synthesis, and biological activity

2021 ◽  
Author(s):  
Robert M. Hohlman ◽  
David H. Sherman
Keyword(s):  
Biological Activity ◽  
Total Synthesis ◽  
Indole Alkaloids ◽  
Recent Advances

This review covers isolation, biological activity, an overview of total synthesis efforts and recent biosynthetic discoveries related to hapalindole-type indole alkaloids.

scholarly journals Total Synthesis of (−)-Vitrenal and Its Biological Activity

1986 ◽  
Vol 59 (6) ◽  
pp. 1897-1900 ◽  
Author(s):  
Mitsuaki Kodama ◽  
Usman S. F. Tambunan ◽  
Tetsuto Tsunoda ◽  
Shô Itô
Keyword(s):  
Biological Activity ◽  
Total Synthesis

ChemInform Abstract: Isolation and Stereostructure of Aurilide, a Novel Cyclodepsipeptide from the Japanese Sea Hare Dolabella auricularia.

ChemInform ◽  
2010 ◽  
Vol 27 (51) ◽  
pp. no-no
Author(s):  
K. SUENAGA ◽  
T. MUTOU ◽  
T. SHIBATA ◽  
T. ITOH ◽  
H. KIGOSHI ◽  
...  
Keyword(s):  
Sea Hare ◽  
Dolabella Auricularia

Significance of C-terminal cysteine modifications to the biological activity of the Saccharomyces cerevisiae a-factor mating pheromone

1991 ◽  
Vol 11 (7) ◽  
pp. 3603-3612
Author(s):  
S Marcus ◽  
G A Caldwell ◽  
D Miller ◽  
C B Xue ◽  
F Naider ◽  
...  
Keyword(s):  
Saccharomyces Cerevisiae ◽  
Biological Activity ◽  
Methyl Ester ◽  
Total Synthesis ◽  
Biologically Active ◽  
Structural Genes ◽  
Wild Type ◽  
Mating Pheromone ◽  
Carboxy Terminal

We have undertaken total synthesis of the Saccharomyces cerevisiae a-factor (NH2-YIIKGVFWDPAC[S-farnesyl]-COOCH3) and several Cys-12 analogs to determine the significance of S-farnesylation and carboxy-terminal methyl esterification to the biological activity of this lipopeptide mating pheromone. Replacement of either the farnesyl group or the carboxy-terminal methyl ester by a hydrogen atom resulted in marked reduction but not total loss of bioactivity as measured by a variety of assays. Moreover, both the farnesyl and methyl ester groups could be replaced by other substituents to produce biologically active analogs. The bioactivity of a-factor decreased as the number of prenyl units on the cysteine sulfur decreased from three to one, and an a-factor analog having the S-farnesyl group replaced by an S-hexadecanyl group was more active than an S-methyl a-factor analog. Thus, with two types of modifications, a-factor activity increased as the S-alkyl group became bulkier and more hydrophobic. MATa cells having deletions of the a-factor structural genes (mfal1 mfa2 mutants) were capable of mating with either sst2 or wild-type MAT alpha cells in the presence of exogenous a-factor, indicating that it is not absolutely essential for MATa cells to actively produce a-factor in order to mate. Various a-factor analogs were found to partially restore mating to these strains as well, and their relative activities in the mating restoration assay were similar to their activities in the other assays used in this study. Mating was not restored by addition of exogenous a-factor to a cross of a wild-type MAT alpha strain and a MATaste6 mutant, indicating a role of the STE6 gene product in mating in addition to its secretion of a-factor.

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