Dataset Information

Synthesis of the C9-C25 Subunit of Spirastrellolide B.

ABSTRACT: The synthesis of the C9-C25 subunit of the marine natural product spirastrellolide B is reported. The key synthetic features included the union of the two key fragments 5 and 6 via a Suzuki-Miyaura coupling reaction and a late-stage, one-pot sequential deprotection/cascade Achmatowicz rearrangement-spiroketalization to install the key spirocyclic intermediate present in the C9-C25 fragment of spirastrellolide B. The synthesis of the C9-C16 fragment 6 was accomplished via a phosphate tether mediated ring-closing metathesis (RCM), a subsequent hydroboration-oxidation protocol, followed by other stereoselective transformations in a facile manner. The spirocyclic intermediate was further functionalized utilizing a Lindlar/NaBH4 reduction protocol to furnish the C9-C25 subunit 3.

SUBMITTER: Maitra S

PROVIDER: S-EPMC4943334 | biostudies-literature | 2016 Jul

REPOSITORIES: biostudies-literature

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Synthesis of the C9-C25 Subunit of Spirastrellolide B.

Maitra Soma S Bodugam Mahipal M Javed Salim S Hanson Paul R PR

Organic letters 20160614 13

The synthesis of the C9-C25 subunit of the marine natural product spirastrellolide B is reported. The key synthetic features included the union of the two key fragments 5 and 6 via a Suzuki-Miyaura coupling reaction and a late-stage, one-pot sequential deprotection/cascade Achmatowicz rearrangement-spiroketalization to install the key spirocyclic intermediate present in the C9-C25 fragment of spirastrellolide B. The synthesis of the C9-C16 fragment 6 was accomplished via a phosphate tether media ...[more]

PMID: 27300267

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Project description:Cis-9, trans-11-conjugated linoleic acid (c9, t11-CLA), a functional fatty acid, is one of the research hotspots in the fields of functional dairy products development because of its multiple beneficial effects in humans and animals. In milk, most c9, t11-CLA is de novo synthesized from trans-11-octadecenoic acid (TVA) and it is confirmed that genes such as stearoyl-coA desaturase 1 (SCD1) play a key role in the synthesis. However, few studies have been reported to deeply elucidate the SCD1-dependent molecular mechanism of cis9, trans11-CLA synthesis and its relationship with the pathways of energy metabolism and lipid metabolism. Therefore, in the present study, MAC-T cells were divided into three groups: CAY group (SCD1-inhibited MAC-T cell model with the addition of CAY, TVA), TVA group (only TVA), and Control group (without CAY, TVA). The relative mRNA expression of SCD1 was measured using real-time PCR, while TVA accumulation and c9, t11 -CLA synthesis were analyzed using gas chromatography (GC). The SCD1-related proteins were firstly screened in MAC-T cells by Tandem Mass Tag (TMT)-based quantitative proteomics analysis, then their functions were annotated by bioinformatic analysis, and finally their relationships with SCD1 were evaluated by parallel reaction monitoring (PRM) analysis and small RNA interference. The results showed that the deficiency of SCD1 led by CAY10566 blocked the synthesis of c9, t11-CLA in MAC-T cells. Sixty-one SCD1-associated proteins were screened and found to be mainly involved in the pathways of energy metabolism and lipid metabolism, such as glycolytic pathway, pentose phosphate pathway, fatty acid elongation pathway, and unsaturated fatty acid biosynthesis. Among these genes, 17 proteins were validated under the PRM analysis. PGAM1 (phosphoglycerate mutase 1), TPI1 (triosephosphate isomerase 1), LDHB (lactate dehydrogenase B), and ALDOA (aldolase, fructose-bisphosphate A) were verified to have a negative relationships with SCD1. This study furthered our understanding of the molecular mechanisms of c9, t11-CLA synthesis in the mammary glands of dairy cows.

Dataset Information

Synthesis of the C9-C25 Subunit of Spirastrellolide B.

Publications

Synthesis of the C9-C25 Subunit of Spirastrellolide B.

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