260. Synthesis of some phosphorylated amino-hydroxy-acids and derived peptides related to the phosphoproteins

Riley, Graham J.; Turnbull, J. H.; Wilson, William E.

doi:10.1039/jr9570001373

Cited by 48 publications

(12 citation statements)

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“…After treatment with sodium hydroxide, glycopeptide A2 lost 64% of its threonine and 45 % of its serine. This would be expected if ,B-carbonyl elimination of an alkoxide bond occurred, and the alkali-treated glycopeptide was shown to contain ac-aminoacrylic acid and a-aminocrotonic acid by spectrophotometric analysis (Price & Greenstein, 1948;Riley, Turnbull & Wilson, 1957;Carubelli, Bhavanandan & Gottschalk, 1965) and by their destruction with strong acids and alkalis (Bergman & Grafe, 1930). If the peptide after treatment with alkali was reduced with sodium borohydride and the peptide hydrolysed and analysed, an increase in the amount of alanine and oc-aminobutyric acid occurred that corresponded to most of the loss of serine and threonine respectively (Tanaka, Bertolini & Pigman, 1964;Tanaka & Pigman, 1965).…”

Section: Discussionmentioning

confidence: 99%

The structure of a glycopeptide isolated from the yeast cell wall

Sentandreu

Northcote

1968

Biochemical Journal

177

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1. Glycopeptides containing mannose were extracted from isolated yeast cell walls by ethylenediamine and purified by treatment with Pronase and fractionation on a Sephadex column. 2. A glycopeptide that appeared homogeneous on electrophoresis and ultracentrifugation had a molecular weight of 76000, and contained a high-molecular-weight mannan and approx. 4% of amino acids. 3. The amino acid composition of the peptide was determined. It was rich in serine and threonine and also contained glucosamine. No cystine and methionine were detected. 4. The glycopeptide underwent a beta-elimination reaction when treated with dilute alkali at low temperatures. The reaction resulted in the release of mannose, mannose disaccharides and possibly other low-molecular-weight mannose oligosaccharides. During the beta-elimination reaction the dehydro derivatives of serine and threonine were formed. One of the linkages between carbohydrate and amino acids in the glycopeptide is an O-mannosyl bond from mannose and mannose oligosaccharides to serine and threonine. 5. After the beta-elimination reaction the bulk of the mannose in the form of the large mannan component was still covalently linked to the peptide. This polysaccharide was therefore attached to the amino acids by a linkage different from the O-mannosyl bonds to serine and threonine that attach the low-molecular-weight sugars. 6. Mannan was prepared from the glycopeptide and from the yeast cell wall by treatment of the fractions with hot solutions of alkali. The mannan contained aspartic acid and glucosamine and some other amino acids. The aspartic acid and glucosamine were present in equimolar amounts; the aspartic acid was the only amino acid present in an amount equivalent to that of glucosamine. Thus there is the possibility of a linkage between the mannan and the peptide via glucosamine and aspartic acid. 7. Mannose 6-phosphate was shown to be part of the mannan structure. Information about the structure of the mannan and the linkage of the glucosamine was obtained by periodate oxidation studies. 8. The glucosamine present in the glycopeptide could not be released by treatment with an enzyme preparation obtained from the gut of Helix pomatia. This enzyme released glucosamine from the intact cell wall. Thus there are probably at least two polymers containing glucosamine in the cell wall. 9. The biosynthesis of the mannan polymer in the yeast cell wall is discussed with regard to the two types of carbohydrate-amino acid linkages found in the glycoprotein.

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Section: Discussionmentioning

confidence: 99%

The structure of a glycopeptide isolated from the yeast cell wall

Sentandreu

Northcote

1968

Biochemical Journal

177

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“…[17] the new trimethylsilyloxy-substituted amino alcohol (R)-13a was produced from -serine [(R)-8] (Scheme 4). The first step in this sequence was the protection of the amino group of -serine [(R)-8] to give carbamate (R)-9, [18] which was esterified with acetyl chloride and methanol to give -serine ester (R)-10. [19] Treatment of (R)-10 with methylmagnesium iodide yielded 1,3-diol (R)-11, the alcohol functionalities of which were then protected to give the bis(trimethylsilyloxy) derivative (R)-12.…”

Section: Amino Alcoholsmentioning

confidence: 99%

A Practical Route to Regiospecifically Substituted (R)- and (S)-Oxazolylphenols

Scheurer¹,

Mosset²,

Bauer³

et al. 2001

Eur. J. Org. Chem.

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Keywords: Amino alcohols / Chirality / Nitrogen heterocycles / Oxazolines / Salicylic acids New, diversely substituted phenolic oxazolines 14a−d and 15a−d were prepared by two complementary routes A and B, starting from salicylic derivatives 4−7 and various enantiomerically pure 1,2-amino alcohols 13a−d. In route A, the 1,2-amino alcohols 13a−d were directly condensed with the salicylic acids 5 and 7, using the Appel reaction, whereas in route B the amino alcohols 13b−d were treated with the 2-hydroxybenzonitriles 4 and 6, under Witte−Seeliger conditions. The latter route was advantageous for L-valinol 13b

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“…Upon saponification of this sirupy ester, N-carbobenzoxy-amino acrylic acid (XIII) (0.7 g, 54%) was obtained; mp 108°; A max = 240 m~(lit. [16] mp 106-108°, A max = 240 mu).…”

Section: I3-elimina Tionmentioning

confidence: 99%