Galacturonic synthesis

Synthesis of Uronic Acids. Part II. 2 3 4-Trimethyl Derivatives of Mannuronic, Glucuronic, and Galacturonic Acids, F. Smith, M. Stacey, and P. I. Wilson, J. Chem. Soc., (1944) 131-134. 

Deoxy-sugars. Part XXI. Synthesis of Some Derivatives of 2-Deoxy-D-galacturonic Acid, W. G. Overend, F. Shafizadeh, and M. Stacey, J. Chem. Soc., (1951) 1487-1489. 

The substrate for HGA synthesis is UDP-D-galacturonic acid (UDP-GalA) (81). UDP-GalA has been isolated from plants (59) and several pathways for its synthesis in planta have been reported (31). In vitro studies on pectin biosynthesis have been hampered since radiolabeled UDP-galacturonic acid is not commercially available. Previous researchers have used several... 

Mitcham, E.J., Gross, K.C., and Wasserman, B.P. (1991) Synthesis of uridinediphospho-[U- C]-D-galacturonic acid by enzyme particulate fractions and purification via high performance liquid chromatography. Phytochem.Anal. 2 112-115. 

L-Ascorbic acid has also been synthesized from D-galacturonic acid —a hexose derivative not so readily available as D-glucose. In addition, several methods have been reported for the synthesis of 1 starting with L-xylose (a pentose not readily available) and cyanide, or with L-threose (a tetrose not readily available) and a two-carbon fragment. 

A cyclic diacetal of this type was employed by Ohle and Berend34ta) and by Link and his coworkers34(b)(o) in the synthesis of D-galacturonic acid. These investigators found that l,2 3,4-diisopropylidene-D-galac-tose was converted by permanganate oxidation in alkaline solution to the... 

A recent screening of various chiral carboxylic acids has allowed the selection of galacturonic derivative 12 as a very efficient control in the stereochemical course of some Passerini reactions (Scheme 1.5). Although the de seems to be strongly dependent on the isocyanide employed, this result suggests the possibility of employing carboxylic acids as easily removable chiral auxiliaries in the asymmetric synthesis of biologically important mandelamides [16]. 

Methyl 2,4-dideoxy-p-L-eryt/zro-hexopyranoside has been obtained as intermediate in the synthesis of 8-hydroxy-p-lysine, from D-galacturonic acid.249... 

C. Niemann and K. P. Link, Synthesis of the hexuronic acids. IV, The synthesis of d-galacturonic acid from D-galacturonic, J. Biol. Chem., 104 (1934) 195-204. 

C. Vogel and P. Gries, Synthesis of 4-amino-4-deoxy-D-galacturonic acid derivative, J. Carbohydr. Chem., 13 (1994) 37-46. 

P. Kovac, J. Hirsch, and V. Kovacik, Synthesis and reactions of uronic acid derivatives. Part II. /8-Elimination reactions of some derivatives of methyl-3,4-0-isopropylidene-D-galacturonate, Carbohydr. Res., 32 (1974) 360-365. 

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