Serinol small molecule - big impact 英文参考文献.docVIP

Andree?enandSteinbüchelAMBExpress2011,1:12 /content/1/1/12 MINI-REVIEW OpenAccess Serinol:smallmolecule-bigimpact Bj?rnAndree?en*andAlexanderSteinbüchel Abstract Theaminoalcoholserinol(2-amino-1,3-propanediol)hasbecomeacommonintermediateforseveralchemical processes.Sincethe1940sserinolwasusedasprecursorforsynthesisofsyntheticantibiotics(chloramphenicol).In thelastyears,newscopesofapplicationswerediscovered.SerinolisusedforX-raycontrastagents, pharmaceuticalsorforchemicalsphingosine/ceramidesynthesis.Itcaneitherbeobtainedbychemicalprocesses basedon2-nitro-1,3-propanediol,dihydroxyacetoneandammonia,dihydroxyacetoneoximeor5-amino-1,3- dioxane,orbiotechnologicalapplicationofaminoalcoholdehydrogenases(AMDH)ortransaminases.Thisreview providesasurveyofsynthesis,propertiesandapplicationsforserinol. Keywords:2-Amino-1,3-propanediol,Aminoalcohol,Serinol Introduction extracts, pyridoxal-5-phosphate, dihydroxyacetone 2-Amino-1,3-propanediol (1,3-dihydroxy-isopropyla- phosphate (D,HAP),andalanine. A Km value of0.1to mine,aminoglycerin oramino-trimethylenglykol) has a 1mMforserinolwasdeterminedforthisenzyme.They molecular formula of C3H9NO2 (Figure 1), belongs to also discovered that glutamine, glutamic, as well as thegroupofaminoalcohols andisprochiral. Asitisa aspartic acid served as amino donors for the transami- structural analogue to the amino acid serine, the com- nasewithsimilar efficiencies. However, theresponsible mon designation is serinol. It is very stable, corrosive, gene and protein for the transamination reaction, hygroscopic, and dissolves very well in water. It has a respectively,havenotbeenunraveledsofar. molecular weight of 91.11 g/mol, melts at 52 to 56 °C, Serinolalsoconstitutesanintermediateinrhizobitox- andhasaboilingpointof115to116°C.Theterm“seri- ine, i. e. 2-amino-4-(2-amino-3-hydropropoxy)- trans- nol”alsodescribesthegroupofC-substitutedcommer- but-3-enoic acid, biosynthesis by the plant pathogen cial analogs. As it is th