Composition and Enzymatic Synthesis of N-Acetylneuraminic Acid (Sialic Acid)

Stimulation of the Production of Neuraminidase in Vibrio cholerae Cultures by N-Acetylmannosamine

“…What may be of great importance is the spatial disposition of the N-acetyl group to C, of N-ANA. Comb & Roseman (1958) showed that the partner with pyruvate in N-ANA is N-acetylmannosamine, not N-acetylglucosamine as previously thought. Our first reaction to the discovery that N-acetylmannosamine stimulated neuraminidase production was to consider the possibility that the N-acetylmannosaniine was converted by the organism to N-ANA which was known to induce neuraminidase (French & Ada, 1959).…”

“…Based on this interpretation, Cornforth, Firth & Gottschalk (1958) were successful in synthesizing from N-acetylglucosamine and oxaloacetic acid a compound which, on physical and chemical grounds, was identical with N-ANA isolated from bovine submaxillary gland mucin. Comb & Roseman (1958) have since shown that an aldolase from Clostridium perfringens breaks down N-ANA, isolated from human plasma, to pyruvate and an N-acetylated hexosamine identified as N-acetylmannosamine. Furthermore, incubation of N-acetylmannosamine and pyruvate with this enzyme yielded a substance which gave the direct Ehrlich reaction and which behaved like N-ANA when chromatographed on paper.…”

“…It seemed therefore appropriate to repeat this work with a basal medium which gave rise to only low titres of neuraminidase, but supported adequate growth of the organism. Furthermore, the results of Comb & Roseman (1958) made it desirable to investigate also the effect of added N-acetylmannosamine and pyruvate. The present paper reports a study of the activities of the N-acetyl derivatives of D-glucosamine, D-mannosamine and D-galactosamine and of D-mannosamine HCl and D-glucosamine HCl.…”

My Mentor- Late Professor Saul Roseman

“…In it's reply when I told him that the word "serendipity" came from the term "Serendeep, or Sarnadeep (in Bengali it means "golden island" of Ceylon) discovered by the king "Bijoy Singha" of Bengal, India (from why were I came from), when all of a sudden he discovered the glittering island of Ceylon from the ship during sunset in the middle of the endless ocean. As we all know that the name "Roseman" became famous overnight in the field of carbohydrate chemistry and biochemistry when he published a one page paper in the JACS (Journal of American Chemical in 1958 [1]. The story I heard many times from him convinced me that every discovery depends on the four M's-"man or woman", "mind", "money", and "moment".…”

Distribution ofN-Acetylneuraminate Lyase in Bacteria and Its Production byEscherichia coli

“…This enzyme can be used as a key enzyme for determining sialic acid (Nacetylneuraminic acid) enzymatically by coupling either lactate dehydrogenase 1 ,2) or pyruvate oxidase. 3 ,4) N-Acetylneuraminate lyase was initially found in some neuraminidase-producing bacteria such as Vibrio cholerae 5 ,6) and Clostridium perjringens, [7][8][9] and also found in Escherichia coli K 235 which produces colominic acid, a homopolymer of N-acetylneuraminic acid. 9 ) Arden et al have studied the distribution of neuraminidase and N-acetylneuraminate lyase activities among corynebacteria, mycobacteria and nocardias, and have shown that the corynebacteria closely related to Corynebacterium diphtheria all produce neuraminidase and Nacetylneuraminate lyase, whereas other cor" ynebacteria, plant pathogeniC corynebacteria, mycobacteria and nocardias lack these two enzyme activities.…”