Production of long-chain hydroxy fatty acids by microbial conversion

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MINI-REVIEW

Production of long-chain hydroxy fatty acids by microbial conversion Yujin Cao & Xiao Zhang

Received: 26 December 2012 / Revised: 24 February 2013 / Accepted: 26 February 2013 / Published online: 14 March 2013 # Springer-Verlag Berlin Heidelberg 2013

Abstract Hydroxy fatty acids (HFAs) are very important chemicals for versatile applications in biodegradable polymer materials and cosmetic and pharmaceutical industries. They are difficult to be synthesized via chemical routes due to the inertness of the fatty acyl chain. In contrast, these fatty acids make up a major class of natural products widespread among bacteria, yeasts, and fungi. A number of microorganisms capable of producing HFAs from fatty acids or vegetable oils have been reported. Therefore, HFAs could be produced by biotechnological strategies, especially by microbial conversion processes. Microorganisms could oxidize fatty acids either at the terminal carbon or inside the acyl chain to produce various HFAs, including α-HFAs, β-HFAs, mid-position HFAs, ω-HFAs, di-HFAs, and tri-HFAs. The enzymes and their encoded genes responsible for the hydroxylation of the carbon chain have been identified and characterized during the past few years. The involved microbes and catalytic mechanisms for the production of different types of HFAs are systematically demonstrated in this review. It provides a better view of HFA biosynthesis and lays the foundation for further industrial production. Keywords Hydroxy fatty acids . Microbial transformation . Catalytic mechanism . Hydroxylase . Monooxygenase

Introduction Hydroxy fatty acids (HFAs) are long-chain fatty acids with one or more hydroxyl groups in their chemical structures. The hydroxyl group may occur at various positions in the Y. Cao (*) : X. Zhang Qingdao Chengyang People’s Hospital, No. 600, Changcheng Road, 266000, Qingdao, China e-mail: [email protected]

carbon chain which can be saturated or unsaturated. HFAs are of great interest because of their special properties compared with ordinary fatty acids, such as much higher viscosity and reactivity (Hou et al. 1999). They are widely used as surfactants, lubricants, cosmetics, antimicrobials, pharmaceutical intermediates, and synthetic precursors in polymer chemistry (Sandoval et al. 2005; Arias et al. 2008). However, most of these fatty acids are not commercially available due to the lack of low cost, practical, and environment-friendly routes for their synthesis. The chemical synthetic pathways for HFAs suffer from various drawbacks, e.g., tedious steps, poor selectivity, and harsh reaction conditions (Liu et al. 2011). Catalysts for specific hydroxylation reaction on the carbon atom of the fatty acyl chain are also limited. These difficulties create hurdles that hamper their commercialization potential. On the other hand, the occurrences and functions of HFAs in the animal and plant kingdoms are well established. Many of these compounds have potential physiological activities and play an important role in stabilizing membrane structures and str