Heptose

A heptose is a monosaccharide with seven carbon atoms.

They have either an aldehyde functional group in position 1 (aldoheptoses) or a ketone functional group in position 2, 3 or 4 (ketoheptoses). Ketoheptoses have 4 chiral centers, whereas aldoheptoses have 5.

Examples

There are few examples of seven-carbon sugars in nature, among which are:

sedoheptulose or D-altro-heptulose (a ketose), an intermediate in the Calvin cycle and in lipid A biosynthesis^[1]^[2]
mannoheptulose (a ketose), found in avocadoes^[3]
L-glycero-D-manno-heptose (an aldose), a late intermediate in lipid A biosynthesis.^[4]

References

^ Horecker, B. L; Smyrniotis, P. Z (1953). "Transaldolase: The Formation of Fructose-6-Phosphate from Sedoheptulose-7-Phosphate". Journal of the American Chemical Society. 75 (8): 2021. doi:10.1021/ja01104a532.
^ Patra, Krushna C; Hay, Nissim (2014). "The pentose phosphate pathway and cancer". Trends in Biochemical Sciences. 39 (8): 347. doi:10.1016/j.tibs.2014.06.005. PMC 4329227. PMID 25037503.
^ Liu, Xuan; Sievert, James; Arpaia, Mary Lu; Madore, Monica A. (2002-01-01). "Postulated Physiological Roles of the Seven-carbon Sugars, Mannoheptulose, and Perseitol in Avocado". Journal of the American Society for Horticultural Science. 127 (1): 108–114. doi:10.21273/JASHS.127.1.108. Retrieved 2018-06-26.
^ Patricia L. Taylor, Kim M. Blakely, Gladys P. de Leon, John R. Walker, Fiona McArthur, Elena Evdokimova, Kun Zhang, Miguel A. Valvano, Gerard D. Wright, Murray S. Junop (1 February 2008). "Structure and Function of Sedoheptulose-7-phosphate Isomerase, a Critical Enzyme for Lipopolysaccharide Biosynthesis and a Target for Antibiotic Adjuvants". Journal of Biological Chemistry. 283 (5): 2835–2845. doi:10.1074/jbc.M706163200. PMID 18056714.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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[1] Horecker, B. L; Smyrniotis, P. Z (1953). "Transaldolase: The Formation of Fructose-6-Phosphate from Sedoheptulose-7-Phosphate". Journal of the American Chemical Society. 75 (8): 2021. doi:10.1021/ja01104a532.

[2] Patra, Krushna C; Hay, Nissim (2014). "The pentose phosphate pathway and cancer". Trends in Biochemical Sciences. 39 (8): 347. doi:10.1016/j.tibs.2014.06.005. PMC 4329227. PMID 25037503.

[AvocadoHeptoses-3] Liu, Xuan; Sievert, James; Arpaia, Mary Lu; Madore, Monica A. (2002-01-01). "Postulated Physiological Roles of the Seven-carbon Sugars, Mannoheptulose, and Perseitol in Avocado". Journal of the American Society for Horticultural Science. 127 (1): 108–114. doi:10.21273/JASHS.127.1.108. Retrieved 2018-06-26.

[Taylor-4] Patricia L. Taylor, Kim M. Blakely, Gladys P. de Leon, John R. Walker, Fiona McArthur, Elena Evdokimova, Kun Zhang, Miguel A. Valvano, Gerard D. Wright, Murray S. Junop (1 February 2008). "Structure and Function of Sedoheptulose-7-phosphate Isomerase, a Critical Enzyme for Lipopolysaccharide Biosynthesis and a Target for Antibiotic Adjuvants". Journal of Biological Chemistry. 283 (5): 2835–2845. doi:10.1074/jbc.M706163200. PMID 18056714.{{cite journal}}: CS1 maint: multiple names: authors list (link)

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