SYNTHESIS OF PHOSPHOLIPID METABOLITES: L-α-GLYCERYLPHOSPHORYL-2-AMINO-2-METHYLPROPANOL

1964 ◽  
Vol 42 (11) ◽  
pp. 1547-1551 ◽  
Author(s):  
Erich Baer ◽  
G. Venkat Rao
Keyword(s):  
Fatty Acid ◽  
Acid Hydrolysis ◽  
Phosphorus Oxychloride ◽  
Barium Salt ◽  
Mild Acid Hydrolysis ◽  
Acid Dichloride ◽  
Catalytic Hydrogenolysis ◽  
Mild Acid

A constituent of and possible intermediate in the metabolism of phosphatidyl-2-amino-2-methylpropanols has been synthesized. The fatty-acid-free moiety, i.e. L-α-glycerylphosphoryl-2-amino-2-methylpropanol, was obtained by phosphorylating D-acetone glycerol with phosphorus oxychloride and quinoline, esterifying the acetone L-α-glycerylphosphoric acid dichloride with N-carbobenzoxy-2-amino-2-methylpropanol in the presence of pyridine, removing the acetone group of acetone L-α-glycerylphosphoryl-N-carbobenzoxy-2-amino-2-methylpropanol by mild acid hydrolysis, and freeing the barium salt of L-α-glycerylphosphoryl-N-carbobenzoxy-2-amino-2-methylpropanol from its protective carbobenzoxy group by catalytic hydrogenolysis.

POLYGLYCERYLPHOSPHORIC ACIDS: I. SYNTHESIS OF BIS(L-α-GLYCERYL) PHOSPHORIC ACID

1958 ◽  
Vol 36 (2) ◽  
pp. 243-248 ◽  
Author(s):  
Erich Baer ◽  
Dmytro Buchnea
Keyword(s):  
Phosphoric Acid ◽  
Acid Hydrolysis ◽  
Intermediate Product ◽  
Phenyl Ester ◽  
Mild Acid Hydrolysis ◽  
Protective Groups ◽  
Catalytic Hydrogenolysis ◽  
Mild Acid

Bis(L-α-glyceryl) phosphoric acid has been prepared by synthesis. It was obtained by phosphorylating D-acetone glycerol with phenylphosphoryl dichloride in the presence of pyridine, and freeing the intermediate product, bis(acetone L-α-glyceryl) phosphoric acid phenyl ester, of its protective groups by catalytic hydrogenolysis and mild acid hydrolysis.

Phosphonolipids. XXIV. Phosphonolipid metabolites. Synthesis of L-α-glyceryl-(N-methyl-2-aminoethyl)phosphonate

1970 ◽  
Vol 48 (9) ◽  
pp. 988-990 ◽  
Author(s):  
Erich Baer ◽  
Sripada K. Pavanaram
Keyword(s):  
Acid Hydrolysis ◽  
Phosphonic Acid ◽  
Mild Acid Hydrolysis ◽  
Catalytic Hydrogenolysis ◽  
Mild Acid

The synthesis of L-α-glyceryl-(N-methyl-2-aminoethyl)phosphonate, a possible intermediate in the biosynthesis and metabolism of L-α-phosphono(N-methyl)cephalins, is described. It was obtained by phosphonylating D-acetone glycerol with (N-carbobenzoxy,N-methyl-2-aminoethyl)phosphonic acid monochloride and triethylamine, and removing the protective isopropylidene and carbobenzoxy groups by mild acid hydrolysis and catalytic hydrogenolysis, respectively.

POLYGLYCERYLPHOSPHORIC ACIDS: I. SYNTHESIS OF BIS(L-α-GLYCERYL) PHOSPHORIC ACID

1958 ◽  
Vol 36 (1) ◽  
pp. 243-248 ◽  
Author(s):  
Erich Baer ◽  
Dmytro Buchnea
Keyword(s):  
Phosphoric Acid ◽  
Acid Hydrolysis ◽  
Intermediate Product ◽  
Phenyl Ester ◽  
Mild Acid Hydrolysis ◽  
Protective Groups ◽  
Catalytic Hydrogenolysis ◽  
Mild Acid

Bis(L-α-glyceryl) phosphoric acid has been prepared by synthesis. It was obtained by phosphorylating D-acetone glycerol with phenylphosphoryl dichloride in the presence of pyridine, and freeing the intermediate product, bis(acetone L-α-glyceryl) phosphoric acid phenyl ester, of its protective groups by catalytic hydrogenolysis and mild acid hydrolysis.

Amino acid sequence of cyanogen bromide fragment CB5 of human hemopexin

1989 ◽  
Vol 54 (3) ◽  
pp. 803-810 ◽  
Author(s):  
Ivan Kluh ◽  
Ladislav Morávek ◽  
Manfred Pavlík
Keyword(s):  
Amino Acid ◽  
Amino Acid Sequence ◽  
Acid Hydrolysis ◽  
Cyanogen Bromide ◽  
Polypeptide Chain ◽  
Amino Acid Residues ◽  
Mild Acid Hydrolysis ◽  
Methionine Residue ◽  
Cyanogen Bromide Fragment ◽  
Mild Acid

Cyanogen bromide fragment CB5 represents the region of the polypeptide chain of hemopexin between the fourth and fifth methionine residue (residues 232-352). It contains 120 amino acid residues in the following sequence: Arg-Cys-Ser-Pro-His-Leu-Val-Leu-Ser-Ala-Leu-Thr-Ser-Asp-Asn-His-Gly-Ala-Thr-Tyr-Ala-Phe-Ser-Gly-Thr-His-Tyr-Trp-Arg-Leu-Asp-Thr-Ser-Arg-Asp-Gly-Trp-His-Ser-Trp-Pro-Ile-Ala-His-Gln-Trp-Pro-Gln-Gly-Pro-Ser-Ala-Val-Asp-Ala-Ala-Phe-Ser-Trp-Glu-Glu-Lys-Leu-Tyr-Leu-Val-Gln-Gly-Thr-Gln-Val-Tyr-Val-Phe-Leu-Thr-Lys-Gly-Gly-Tyr-Thr-Leu-Val-Ser-Gly-Tyr-Pro-Lys-Arg-Leu-Glu-Lys-Glu-Val-Gly-Thr-Pro-His-Gly-Ile-Ile-Leu-Asp-Ser-Val-Asp-Ala-Ala-Phe-Ile-Cys-Pro-Gly-Ser-Ser-Arg-Leu-His-Ile-Met. The sequence was derived from the data on peptides prepared by cleavage of fragment CB5 by mild acid hydrolysis, by trypsin and chymotrypsin.

The synthesis of a carbohydrate-like dihydrooxazine and tetrahydrooxazine as putative inhibitors of glycoside hydrolases: A direct synthesis of isofagomine

2002 ◽  
Vol 80 (8) ◽  
pp. 857-865 ◽  
Author(s):  
Wayne M Best ◽  
James M Macdonald ◽  
Brian W Skelton ◽  
Robert V Stick ◽  
D Matthew G Tilbrook ◽  
...  
Keyword(s):  
Direct Synthesis ◽  
Glycoside Hydrolases ◽  
Crystalline Solid ◽  
Glycosidase Inhibitors ◽  
Protecting Group ◽  
Mild Acid Hydrolysis ◽  
Catalytic Hydrogenolysis ◽  
Palladium On Carbon ◽  
Mild Acid

The treatment of benzyl 2,3-O-isopropylidene-β-L-xylopyranoside with N-hydroxyphthalimide under Mitsunobu conditions, followed by protecting-group interchange, gave benzyl 4-O-[(tert-butoxycarbonyl)amino]-2,3- O-isopropylidene-α-D-arabinoside. Mild acid hydrolysis and catalytic hydrogenolysis afforded 4-O-[(tert-butoxycarbonyl)amino]-D-arabinose that, upon heating in water, gave the dihydrooxazine [(4R,5S,6R)-5,6-dihydro-4,5-dihydroxy-6-hydroxymethyl-4H-1,2-oxazine] as a crystalline solid. A single-crystal structure determination of this solid showed it to exist in the 5H6 conformation. Reduction of the dihydrooxazine gave the tetrahydrooxazine [(4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-3,4,5,6-tetrahydro-2H-1,2-oxazine]. The dihydrooxazine was an effective inhibitor of two β-glucosidases (Ki = 27 and 35 µM). Benzyl 2,3-O-isopropylidene-β-L-xylopyranoside, via the derived imidazylate, was converted into a nitrile that, upon reduction and protecting-group manipulations, gave benzyl 4-C-aminomethyl-4-deoxy-α-D-arabinoside. Treatment of this amine with hydrogen and palladium-on-carbon gave isofagomine.Key words: dihydrooxazine, tetrahydrooxazine, isofagomine, iminosugars, glycosidase inhibitors.

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