Dolbier HW Solutions 639

Dolbier HW Solutions 639 - The problem states that PGE 2...

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The order of decreasing sequence rule precedence is When the three-dimensional formula is viewed from a perspective in which the lowest ranked sub- stituent is away from us, we see The absolute con f guration is R . The conversion of L -glycerol 3-phosphate to a phosphatidic acid does not affect any of the bonds to the stereogenic center, nor does it alter the sequence rule ranking of the substituents. The absolute con f guration is R . 26.5 Cetyl palmitate (hexadecyl hexadecanoate) is an ester in which both the acyl group and the alkyl group contain 16 carbon atoms. 26.6 The structure of PGE 1 is found in text Figure 26.5.
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Unformatted text preview: The problem states that PGE 2 has one more double bond than PGE 1 and that it is biosynthesized from arachidonic acid. Arachidonic acid (text Table 26.1) has a double bond at C-5, and thus PGE 2 has the structure shown. several steps Arachidonic acid 5 CH 3 COOH PGE 2 OH CH 3 COOH HO O 5 HO O COOH OH CH 3 PGE 1 CH 3 (CH 2 ) 14 CO(CH 2 ) 15 CH 3 O Hexadecyl hexadecanoate C CH 2 OCR H R 9 CO H 2 O 3 POCH 2 H 2 O 3 POCH 2 O R 9 CO O O . . . RCOCH 2 O H HOCH 2 OH C H 2 O 3 POCH 2 Order of decreasing rank is clockwise, therefore R . HO H H 2 O 3 POCH 2 HOCH 2 . . . LIPIDS 733...
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