In 2004,Peng, Sheng; McGinley, Chris M.; Van der Donk, Wilfred A. published 《Synthesis of Site-Specifically Labeled Arachidonic Acids as Mechanistic Probes for Prostaglandin H Synthase》.Organic Letters published the findings.Reference of Methyl 3-hydroxypropanoate The information in the text is summarized as follows:
Prostaglandin H synthase catalyzes the first committed step in the biosynthesis of prostaglandins and thromboxane. Herein we report the synthesis of four site-specifically labeled arachidonic acids (all Z)-HO2C(CH2)3CH:CHCH:CHCR12X:CHCR22CH:Y(CH2)4Me (I, R1 = D, R2 = H, X = 12CH, Y = CH; R1 = R2 = H, X = 13CH, Y = CH; R1 = H, R2 = D, X = 12CH, Y = CH; R1 = R2 = H, X = CH, Y = 13CH) for investigation of the radical intermediate formed during this enzymic reaction. Two compounds, I (R1 = D, R2 = H, X = 12CH, Y = CH; R1 = R2 = H, X = 13CH, Y = CH), were prepared using a common C9-C11 fragment Me3CMe2SiOCH2CD2CHO, while another target, I (R1 = R2 = H, X = CH, Y = 13CH) was synthesized using a previously reported advanced intermediate, (Z,Z)-MeO2C(CH2)3CH:CHCH2CH:CHCH2CHO. An alkyne coupling of 1-heptyne with BrCD2CCCH2CH2OSiPh2CMe3 followed by hydrogenation and Wittig reaction was used to prepare the final labeled substrate, I (R1 = H, R2 = D, X = 12CH, Y = CH). In the part of experimental materials, we found many familiar compounds, such as Methyl 3-hydroxypropanoate(cas: 6149-41-3Reference of Methyl 3-hydroxypropanoate)
Methyl 3-hydroxypropanoate(cas: 6149-41-3) belongs to esters with low molecular weight are commonly used as fragrances and found in essential oils and pheromones. Their flexibility and low polarity is manifested in their physical properties; they tend to be less rigid (lower melting point) and more volatile (lower boiling point) than the corresponding amides. Reference of Methyl 3-hydroxypropanoate
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