Total synthesis of sporidesmolide I

Shemyakin, M. M.; Ovchinnikov, Yu.A.; Иванов, В. Т.; Kiryushkin, A. A.

doi:10.1016/s0040-4020(01)99354-8

Cited by 28 publications

(9 citation statements)

References 13 publications

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“…When P. chartarum was grown on potato+carrot extract to which optically inactive isoleucine had been added, its production of sporidesmolide I was inhibited, and the only compound that could be isolated was 2 for which in this paper the name sporidesmolide I1 is retained (Bertaud, Probine, Shannon & Taylor, 1965). Sporidesmolide I1 has been synthesized (Shemyakin et al 1965), thus providing further confirmation that the isoleucine residue has the threo-D-configuration. A third compound, sporidesmolide 111, is formed in small amount by P. chartarum growing on potato +carrot extract, and was shown to have structure 3 (Russell, MacDonald & Shannon, 1964).…”

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confidence: 63%

“…Four When P. chartarum was grown in liquid surface culture on potato +carrot extract it formed mainly sporidesmolide I. This was shown by chemical degradation to be 1, a structure which has since been confirmed by synthesis (Shemyakin et al 1965). A second component was also present which, although it was not isolated, was named sporidesmolide I1 and was tentatively assigned a structure in which the D-valine residue of 1 was replaced by a residue of a D-isoleucine isomer (Russell, 1960a(Russell, , 1962.…”

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confidence: 94%

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Effects of Stereoisomeric Isoleucines on Sporidesmolide Biosynthesis by Pithomyces chartarum

Russell

1967

Journal of General Microbiology

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SUMMARYAs well as the known sporidesmolides I, I1 and 111, Pithomyces chartarum produces sporidesmolides or similar compounds which contain residues of erythro-isoleucine and a-hydroxyisocaproic acid. When erythro-L-isoleucine was added to the growth medium, synthesis of sporidesmolides I and I11 was inhibited and synthesis of isoleucine-containing sporidesmolides, mainly sporidesmolide 11, was promoted. Threo-L-isoleucine in the medium was poorly utilized, but its presence resulted in production of a very complex mixture of sporidesmolides containing a higher proportion of isoleucine residues than the control. Epimerization of erythro-D-isoleucine occurred in the medium. Neither epimer was well utilized, and this isomer had little effect on sporidesmolide production or composition ; it promoted some increase in the synthesis of isoleucine-containing sporidesmolides. Threo-Disoleucine had effects qualitatively similar to but less pronounced than those of erythro-L-isoleucine, probably because of extracellular epimerization. The use of epimeric pairs of amino acids as tools for investigating biochemical processes involving inversion of configuration at an amino acid a-carbon atom is suggested.

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confidence: 63%

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confidence: 94%

Effects of Stereoisomeric Isoleucines on Sporidesmolide Biosynthesis by Pithomyces chartarum

Russell

1967

Journal of General Microbiology

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“…Harris and Strommen (1972) have shown the early development of front-back discriminations, as compared with left-right. There is also evidence from some Soviet psychologists that children who have been forced to spend long periods in bed due to illness show greater decrement in spatial discriminations involving mixed levels of transformation, e.g., ' upper right or lower left ' (Shemyakin, 1959). Consequently, the literature to date was tabulated according to whether the authors had used recognition or inference procedures, and on the spatial position that the child was required to predict.…”

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confidence: 99%

Recognition and Inference in the Co‐ordination of Perspectives

Eiser¹

1974

Brit J of Edu Psychol

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Summary. Previous research on the child's ability to predict the viewpoint of another has typically used either (a) a recognition procedure, in which the subject views the model from different perspectives prior to selecting the viewpoint required, or (b) an inference procedure, in which the subject makes his choice after viewing the model from one position only. An experiment is reported which directly compares the effects of these two procedures, and demonstrates less egocentrism in a recognition than in an inference condition. It is suggested that this distinction can help explain some apparent anomalies in the results of earlier research.

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“…P-Malamidic acid was converted to its benzyl ester (A) by reacting its cesium salt with benzyl bromide (1 5). Boc-glutamine was coupled to the free hydroxyl group of pmalamidic acid benzyl ester; the coupling was 36 carried out by reaction with benzenesulfonyl chloride in pyridine (16) and also with N,"carbonyldiimidazole (1 7). The product (B) was subject to hydrogenolysis over Pd/C catalyst to obtain Boc-Gln-Mal-OH (C).…”

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confidence: 99%

Biofunctional evaluation of a hydrogen bond stabilizing the conformation in the cyclic part of oxytocin

Roy

Gazis

Shakman

et al. 1982

International Journal of Peptide and Protein Research

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[5‐β‐Malamidic acid] oxytocin was synthesized to study the importance of the hydrogen bond between the C=O of Tyr2 and the peptide N‐H of Asn5 for the stabilization of a biologically functional conformation of oxytocin. This analog lacks the peptide N‐H at residue 5 required for the formation of a hydrogen bond with the C=O of Tyr2. [5‐β‐Malamidic acid] oxytocin exhibited 45.1 ± 2.5 U/mg and 65.6 ± 5.9 U/mg of uterotonic activity, in vitro, in the absence and in the presence, respectively, of Mg2+, 147 ± 14 U/mg of uterotonic activity in vivo, 203 ± 13 U/mg of milk‐ejecting activity, 0.37 ± 0.03 U/mg of pressor activity and 0.32 ± 0.29 U/mg of antidiuretic activity. It is concluded that devoid of the hydrogen bond under question, an oxytocin‐like peptide can still assume the conformation needed to interact with the oxytocin receptors.

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Total synthesis of sporidesmolide I

Cited by 28 publications

References 13 publications

Effects of Stereoisomeric Isoleucines on Sporidesmolide Biosynthesis by Pithomyces chartarum

Effects of Stereoisomeric Isoleucines on Sporidesmolide Biosynthesis by Pithomyces chartarum

Recognition and Inference in the Co‐ordination of Perspectives

Biofunctional evaluation of a hydrogen bond stabilizing the conformation in the cyclic part of oxytocin

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