Synthesis of 6-deoxy-6-sulfo-α-d-glucopyranosyl phosphate

Hoch, Monika; Heinz, Ernst; Schmidt, Richard R.

doi:10.1016/0008-6215(89)85043-8

Cited by 41 publications

(19 citation statements)

References 22 publications

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“…[26,27] The obtained material was completely unprotected at the hydroxy functions to give a tris(cyclohexylammonium) salt instead of the usually used triethylammonium salt. Coupling of 2 and 3 formed uridine the cycloSal-triester no protection at the sugar hydroxy groups was necessary.…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Nonnatural Nucleoside Diphosphate Sugars

Wolf¹,

Berrio²,

Meier³

2011

Eur J Org Chem

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Recently, we reported an efficient chemical method for the synthesis of a variety of naturally occurring nucleoside diphosphate (NDP) sugars. This method, which is based on the cycloSal approach, can also be used, in principle, for the preparation of rare or even nonnatural NDP sugars. Herein, the syntheses of sulfoquinovose‐, glucose‐6‐sulfate‐, L‐galactose‐, and 2‐fluoroglycopyranoside‐containing NDP sugars are presented, as well as the synthesis of NDP sugars with non‐natural nucleosides. The reactions described gavestereoisomerically defined NDP sugars in high yields and short reaction times.

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Section: Resultsmentioning

confidence: 99%

Synthesis of Nonnatural Nucleoside Diphosphate Sugars

Wolf¹,

Berrio²,

Meier³

2011

Eur J Org Chem

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“…; Waters, Mieford, Mass., USA) exactly as described before (Rossak et al 1995). Reference compounds such as UDPS, ADPS, CDPS, GDPS, sulfoquinovose-1-phosphate (SQVP) and sulfoquinovose (SQV) were avalaible from previous work Hoch et al 1989). Enzymatic degradation of the isolated compounds by nucleotide pyrophosphatase followed by alkaline phosphatase has already been described (Rossak et al 1995).…”

Section: Methodsmentioning

confidence: 99%

Uridine-diphospho-sulfoquinovose: diacylglycerol sulfoquinovosyltransferase activity is concentrated in the inner membrane of chloroplast envelopes

Tietje

Heinz

1998

Planta

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In experiments on the assembly of the sulfolipid sulfoquinovosyl diacylglycerol in envelope membranes of chloroplasts, UDP-sulfoquinovose (UDPS) was used with highest eciency, and the corresponding enzyme, UDP-sulfoquinovose:diacylglycerol sulfoquinovosyltransferase, was partially characterized (E. , Eur J Biochem 184: 445±453). Here, we identi®ed 35 S-and 33 P-labelled UDPS from various photosynthetically active organisms, suggesting that the sulfosugar nucleotide used for sulfolipid biosynthesis throughout the plant kingdom, including phototrophic bacteria, may indeed be UDPS. For attribution of the sulfolipid synthase to one of the two plastidial envelope membranes, these membranes were isolated from pea and spinach chloroplasts. The sulfoquinovosyltransferase was localized in the inner membrane of envelopes, which also contains the competing UDP-galactose:diacylglycerol galactosyltransferase. In contrast to the sulfoquinovosyltransferase, a substantial proportion of the galactosyltransferase was found in the outer membranes of envelopes from pea chloroplasts.

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“…High Performance Liquid Chromatography of Synthetic Sulfosugar and Nucleotide Standards-Different sulfoquinovose nucleotide standards as well as sulfoquinovose 1-phosphate were available from a previous chemical synthesis (7,21). Sulfoquinovose was prepared from synthetic sulfoquinovose 1-phosphate by acid hydrolysis with 1 M aqueous hydrochloric acid for 1 h at 90°C followed by vacuum drying.…”

Section: Methodsmentioning

confidence: 99%