152899-14-4

Upstream product

• 152899-13-3 (4S)-4-benzyl-3-octanoyl-1,3-oxazolidin-2-one 
• 74-88-4 methyl iodide 
• 111-64-8 n-octanoic acid chloride 
• 63-91-2 L-phenylalanine 
• 152899-15-5 <3(2'R),4S>-3-(2-Methyl-1-oxooctyl)-4-(phenylmethyl)-2-oxazolidinone 
• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 
• 87877-11-0 Phe-Chlor 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 3081-24-1 H-Phe-OEt 
• 3182-95-4 L-Phenylalaninol 

Downstream Products

• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 116013-69-5 (2S)-2-methyloctan-1-ol 
• 3004-93-1 (2S)-2-Methyl-octanoic acid 
• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 
• 117184-53-9 6'-epi-Aranorosin 
• 117184-53-9 Epiaranorosin 
• 153077-11-3 Ethyl (2S,2'E,4'E,6'S)-2-(4,6-dimethyldodeca-2,4-dienoylamido)-3-(4-hydroxyphenyl)propanoate 
• 153077-12-4 (2E,4E)-(S)-4,6-Dimethyl-dodeca-2,4-dienoic acid [(S)-1-formyl-2-(4-hydroxy-phenyl)-ethyl]-amide 
• 7786-29-0 (S)-α-methyloctanal 

Relevant academic research and scientific papers

Understanding Programming of Fungal Iterative Polyketide Synthases: The Biochemical Basis for Regioselectivity by the Methyltransferase Domain in the Lovastatin Megasynthase

Highly reducing polyketide synthases (HR-PKSs) from fungi synthesize complex natural products using a single set of domains in a highly programmed, iterative fashion. The most enigmatic feature of HR-PKSs is how tailoring domains function selectively during different iterations of chain elongation to afford structural diversity. Using the lovastatin nonaketide synthase LovB as a model system and a variety of acyl substrates, we characterized the substrate specificity of the LovB methyltransferase (MT) domain. We showed that, while the MT domain displays methylation activity toward different β-ketoacyl groups, it is exceptionally selective toward its naturally programmed β-keto-dienyltetraketide substrate with respect to both chain length and functionalization. Accompanying characterization of the ketoreductase (KR) domain displays broader substrate specificity toward different β-ketoacyl groups. Our studies indicate that selective modifications by tailoring domains, such as the MTs, are achieved by higher kinetic efficiency on a particular substrate relative to the rate of transformation by other competing domains.

Volatile methyl esters of medium chain length from the bacterium Chitinophaga Fx7914

The analysis of the volatiles released by the novel bacterial isolate Chitinophaga Fx7914 revealed the presence of ca. 200 compounds including different methyl esters. These esters comprise monomethyl- and dimethyl-branched, saturated, and unsaturated fatty acid methyl esters that have not been described as bacterial volatiles before. More than 30 esters of medium C-chain length were identified, which belong to five main classes, methyl (S)-2-methylalkanoates (class A), methyl (S)-2,(ω-1)-dimethylalkanoates (class B), methyl 2,(ω-2)-dimethylalkanoates (class C), methyl (E)-2-methylalk-2-enoates (class D), and methyl (E)-2,(ω-1)-dimethylalk-2- enoates (class E). The structures of the compounds were verified by GC/MS analysis and synthesis of the target compounds as methyl (S)-2-methyloctanoate (28), methyl (S)-2,7-dimethyloctanoate ((S)-43), methyl 2,6-dimethyloctanoate (49), methyl (E)-2-methylnon-2-enoate (20a), and methyl (E)-2,7-dimethyloct-2- enoate (41a). Furthermore, the natural saturated 2-methyl-branched methyl esters showed (S)-configuration as confirmed by GC/MS experiments using chiral phases. Additionally, the biosynthetic pathway leading to the methyl esters was investigated by feeding experiments with labeled precursors. The Me group at C(2) is introduced by propanoate incorporation, while the methyl ester is formed from the respective carboxylic acid by a methyltransferase using S-adenosylmethionine (SAM).

Total synthesis of emericellamides A and B

The total synthesis of emericellamides A and B is reported. A convergent, flexible strategy employing peptide chemistry, asymmetric alkylations, and culminating in macrolactamization is described. The previously reported structure of both compounds is confirmed.

Isolation and total synthesis of gymnastatin N, a POLO-like kinase 1 active constituent from the fungus Arachniotus punctatus

A high throughput screen against POLO-like kinase 1 (Plk1), an anti-cancer target, identified an active extract from the fungus Arachniotus punctatus. Bioassay guided fractionation led to the isolation of the new natural product, gymnastatin N (1) and the known compound aranorosinol A (2) with IC50 values of 13 and 118 μM, respectively. A 12′-hydroxy analog of gymnastatin N, 3, was also isolated as a minor component. Gymnastatin N (1) was found to be a 52:48 mixture of (1S,6′R) and (1R,6′R) diastereomers, by synthesis of the four possible diastereomers and comparison of the optical rotation and chiral HPLC profile of each diastereoisomer with the natural product. Analogues of 1 were synthesized and evaluated against the Plk1 assay and these SAR studies suggested that the diene and free carboxylic acid moieties might be responsible for its bioactivity. Graphical Abstract.

An efficient strategy for the synthesis of chiral liquid crystals using Evans' methodology

The synthesis of liquid crystal compound 2 was achieved using Evans' methodology. The strategy was based on three key synthetic reactions: alkylation of chiral amide enolates, Mitsunobu and, finally, esterification. The final compound presents a stable smectic A phase.

Tumor chemopreventive activity of 3-O-acylated (-)-epigallocatechins

In order to seek promising cancer chemopreventive agents, we assessed the antitumor promoting activities of 3-O-octanoyl- or 3-O-(2-methyloctanoyl)-(-)- epigallocatechins, inhibiting markedly the activation of Epstein-Barr virus early antigen, in a two-stage mouse skin carcinogenesis assay. As a result, these derivatives inhibited a papilloma formation 1.3-1.6-fold more strongly than (-)-epigallocatechin gallate well established as anti-tumor promoter.

The total synthesis of the diepoxycyclohexanone antibiotic aranorosin and novel synthetic analogues

A short synthesis of the novel antibiotic aranorosin in chiral form is described which employs (i) a novel hypervalent iodine-mediated oxidative hydroxylation of a tyrosinal derivative and (ii) a stereocontrolled cis-bisepoxidation in the key steps. A similar procedure was employed to prepare 6′-epiaranorosin, and hence establish the stereochemistry of the natural compound, and to prepare novel aranorosin analogues. An organometallic route is described which gives desamidoaranorosin.

Total synthesis and structure assignment of the antitumor antibiotic aranorosin

The structurally unique antifungal and antitumor antibiotic aranorosin was prepared in a convergent, stereoselective sequence. Oxidative cyclization of N-protected L-tyrosine, followed by face-selective 1,2-addition of [(benzyloxy)methyl]lithium, Henbest oxidation in the presence of Kishi's radical inhibitor, and simultaneous N,O-deprotection led to an amino diol which was N-acylated with the fatty acid side-chain segment. After a low-temperature reduction of the lactone moiety to the lactol, the carbonyl function was regenerated under neutral conditions by diol cleavage with sodium periodate. Preparation of the acid side chain involved a diastereoselective imide α-alkylation directed by Evans' oxazolidinone auxiliary, followed by a series of Wittig-Horner chain extensions. Since the relative configuration at the C(6') position of the natural product had not been determined, we prepared both the (6'S) and the (6'R) isomers of aranorosin. Comparison of synthetic material with the reported spectral data for natural (-)-aranorosin, especially 1H and 13C NMR and [α](D), did not allow a definitive assignment. After purification of a sample of the isolated material from Pseudoarachniotus roseus the corrected [α](D) strongly indicated the (6'R)-stereochemistry for the natural compound. This assignment was confirmed by circular dichroism spectra for (6'S)- and (6'R)-aranorosin and the natural material.