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 (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.

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 (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.

Impact of Air‐frying on The Plasmalogens Deterioration and Oxidation in Oyster Revealed by Mild Acid Hydrolysis and HILIC‐MS based Lipidomics Analysis

2021 ◽  
Author(s):  
Weibo Lu ◽  
Min Zhang ◽  
Ting Zhang ◽  
Qingchen Wang ◽  
Jie Wang ◽  
...  
Keyword(s):  
Acid Hydrolysis ◽  
Mild Acid Hydrolysis ◽  
Mild Acid

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.

Selective cleavage and anticoagulant activity of a sulfated fucan: stereospecific removal of a 2-sulfate ester from the polysaccharide by mild acid hydrolysis, preparation of oligosaccharides, and heparin cofactor II–dependent anticoagulant activity

Glycobiology ◽  
2004 ◽  
Vol 15 (4) ◽  
pp. 369-381 ◽  
Author(s):  
Vitor H. Pomin ◽  
Mariana S. Pereira ◽  
Ana-Paula Valente ◽  
Douglas M. Tollefsen ◽  
Mauro S. G. Pavão ◽  
...  
Keyword(s):  
Acid Hydrolysis ◽  
Anticoagulant Activity ◽  
Sulfate Ester ◽  
Mild Acid Hydrolysis ◽  
Heparin Cofactor Ii ◽  
Sulfated Fucan ◽  
Mild Acid
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