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A decrease in moisture absorption–retention capacity of N-deacetylation of hyaluronic acid

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The linear non-sulfated glycosaminoglycan, hyaluronic acid (HA), is widely distributed throughout connective, epithelial and neural tissues etc., and is of great importance in tissue hydration, lubrication and cellular function. Along with the age growth, HA will lose its acetyl groups under action of HA N-deacetylase in vivo. However, the biological consequence of this physiological process remains largely unknown. Herein two highly N-deacetylated HAs, dHA-6 and dHA-10 were generated via the NH2NH2-HIO3 procedure. Their molecular weights were estimated to be 24 and 16 kDa by high performance gel-permeation chromatography (HPGPC), and the N-deacetylation degrees were 79.4 % and 93 % respectively, as determined by 1H nuclear magnetic resonance (NMR). The study on moisture-absorption (Ra) and -retention (Rh) abilities demonstrated that the Ra values of dHAs under conditions of 81 % or 43 % relative humidity, as well as the Rh values of dHAs under dry condition or 43 % relative humidity, were significantly smaller than that of their respective re-N-acetylated products. The decline of moisture-absorption and –retention capacity after HA N-deacetylation were consistent with the appearance of unsolvated amides remained in the N-deacetylated products, as indicated by circular dichroism (CD) spectroscopy. Our findings implied that HA N-deacetylation, in addition to the decrease of HA contents in the elderly persons, might account for manifestations of naturally aged skin, such as laxity, sagging, and wrinkling.

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hyaluronic acid


circular dichroism


relative humidity

Ra :

moisture-absorption abilities

Rh :

moisture-retention abilities


high performance gel-permeation chromatography


nuclear magnetic resonance


HA N-deacetylated product resulted from 6 h of hydrazinolysis


HA N-deacetylated product resulted from 10 h of hydrazinolysis


re-N-acetylated product of dHA-6


re-N-acetylated product of dHA-10


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This work was supported by the National Science Foundation of China (NSFC) [Grant No. 31270860 to J.D] and the “Interdisciplinary Cooperation Team” Program for Science and Technology Innovation of the Chinese Academy of Sciences.

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Correspondence to Jinyou Duan or Shunchun Wang.

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Zhang, W., Mu, H., Zhang, A. et al. A decrease in moisture absorption–retention capacity of N-deacetylation of hyaluronic acid. Glycoconj J 30, 577–583 (2013).

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