j1939 Index a N-acetylneuraminate lyase 172, 478, 1640 a-acetolactate 991, 992 N-acetylneuraminic acid 865 a-amino acid dehydrogenases 6, 1166 N-acetylneuraminic acid aldolase (NeuA) 864 a-amino-e-caprolactam racemase 1614–1617 – natural substrates 865 a-aspartyl dipeptidase 754 – prediction, three-point binding model absorbable organic chlorides (AOX) 1824 for 869 abzyme 9A8 1743 3-acetyloctanal 934 abzymes Achromobacter obae 837, 1614 – based therapy 1737 Achromobacter xylosoxidans 1590 – mediated cell death 1753 acid–base catalysis 967 – mediated generation of peroxide 1737 acid–base chemistry 103 – in non-aqueous solutions 1770 acid phosphatases ACE inhibitors 336, 1215 – dephosphorylation by 1016, 1017 acetaldehyde 1022 ––mechanism 1018 – carboligation 923 – formation of DHAP 1020, 1021 acetaldehyde-dependent aldolases 861 – one-pot cascade reaction involving acetamidase/formamidase protein with 1024 family 613 – phosphorylation, mechanism of 1018 N-acetamidomalonate esters, alkylation 577 – structural and mechanistic acetic acid bacteria 1369 description 1013–1016 acetobacter 17 – transphosphorylation by 1017–1019 acetohydroxyacid synthase (AHAS) 920, 924 Acinetobacter calcoaceticus 1097, 1410, – from Escherichia coli, isoenzymes 926 1556, 1557 acetolactate decarboxylase 992 aconitase (Acn) 467, 476 acetolactate formation 796, 850, 927 acrylamide 522 acetonitrile, reaction medium 625 – synthesis 522 O-acetylated cis-azetidinone 287 acrylate esters 1149 acetylcholine hydrolysis by carbamates, acrylates 1149 inhibition of 1744 acrylonitrile hydration, disadvantages 523 acetylcholinesterase 1743 acyclic carboxylates, hydrolysis of 298, 299 N-acetyl-D-glucosamine 996 acyclic 1,2-diketones 936 N-acetyl-D,L-3-(4-thiazolyl)alanine 834 N-acylamino acid racemase 1630, 1631 N-acetyl-D-neuraminic acid aldolase 995 acylase process 575 acetylene hydratase 471 acylation 339 – contains tungsten atom 472 – of monohydroxy compounds 328 O-acetyl 5-hydroxyhexanenitrile 288 acyl carrier protein (ACP) 486, 487 N-acetylneuraminate (NeuNAc) acyl-CoA-derivative 62 aldolase 864–872 acyl-CoA thioesterases 765 Enzyme Catalysis in Organic Synthesis, Third Edition. Edited by Karlheinz Drauz, Harald Gröger, and Oliver May. Ó 2012 Wiley-VCH Verlag GmbH & Co. KGaA. Published 2012 by Wiley-VCH Verlag GmbH & Co. KGaA. 1940j Index N-acyl compounds 571 3a-hydroxysteroid dehydrogenase acyl donor esters 726–729 (HSDH) 1094 acyl-enzyme complex 691 a-keto acids, biocatalytic reductive amination N-acylglucosamine 2-epimerase 865, 1637, of 17 1640, 1641 a-keto acid trimethylpyruvate (2-oxo-3, 2-acyl-2-hydroxy acids 930 3-dimethylbutyric acid 1183 acyloin condensations 920–931, a-keto-b-hydroxyisovalerate 1189 1709, 1710 a-ketoglutarate 1572, 1578 – 2-acyl-2-hydroxy acids 930 – reaction mechanism 1575 – acyloin condensations 920–931 a-ketoglutarate-dependent – aliphatic acyloins 929 hydroxylases 1572 – aliphatic–aromatic acyloins 924–927 a-ketoglutarate transaminase 796 – with aliphatic donor aldehydes, and aromatic Ajinomoto Co. Inc. 31, 662, 997, 1628 acceptors 924–927 Alangium lamarckii 770 – araliphatic–aliphatic acyloins 928, 929 D-alanine amidase 602, 605 – aromatic donors, and aliphatic acceptors alanine aminotransferase 781, 1620, 1865 carboligation 927, 928 alanine dehydrogenase 800, 1167, 1187, – enzymatic acyloin condensations 1188, 1835, 1928 chemoselectivity 922, 923 DL-alanine methyl ester 600, 605 – enzymatic acyloin condensations D-alanine oligomers 595 stereoselectivity 923, 924 alanine racemase 1610, 1611 – with formaldehyde and formaldehyde alanine-scanning mutagenesis 1746 synthons 936–938 b-alanyl CoA ammonia lyase 764, 765 – with ketones and imines 935, 936 – reactions catalyzed by 765 – olefinic aliphatic and araliphatic alcohol dehydrogenases (ADHs) 6, 12, 33, 34, acyloins 929, 930 53, 61, 364, 366, 383, 386, 407, 1037, 1039, – racemic resolution via lyase/ligase 1050, 1138, 1205, 1215, 1326–1341, 1327, reactions 938–940 1407, 1592, 1888, 1928, 1935 – Stetter-type reactions 933–935 – bi-enzymatic deracemization 1389 – sugar derivatives 930, 931 – as biocatalysts 1038, 1040 – umpolung reactions, in chemistry and – commonly used 1328 biology 919–920 – glycerol dehydrogenases (GDHs) 1331–1334 acyltransferases 323, 710, 1700, 1701 – Horse liver alcohol dehydrogenase adenosine 50-triphosphate (ATP) 1006 (HLADH) 1328–1330 – enzymes used in regeneration of – Lactobacillus kefir 1334 1007–1009 – lyophilized Rhodococcus ruber expressing, adenosylcobalamin (AdoCbl). See vitamin B12 kinetic resolutions 1332, 1333 þ S-adenosylmethionine-dependent – NAD(P) regeneration systems 1335–1338 fluorinase 1578 – nicotinamide-dependent 52 S-adenosylmethionine-dependent – non-enzymatic approaches 1338–1341 halogenases 1573 – overexpressed form 1053 S-adenosylmethionine-dependent – oxidase-catalyzed kinetic resolution 1390 methyltransferases 1575, 1578, 1579 – oxidation mechanism 1327 adenylosuccinate lyase 754, 755 – oxidation of aldehydes 1408 adipodiamide 521, 522, 822 – from Rhodococcus ruber 1331 adipodinitrile 822 – screening methods to obtain novel 1049 adrenodoxin reductase (AdR) 1256, 1257 – short-chain zinc-independent 1407 Agrobacterium radiobacter 150, 370, 373, 388, – sources, useful for biocatalysis 1042–1049 399, 1126, 1129 – substrates and kinetic constants for 1411, Agrobacterium tumefaciens 433, 660, 1178, 1412 1179, 1388, 1641 – substrate spectra of 1328 Agrocybe aegerita 1233, 1555, 1559 – Sulfolobus solfataricus 1330 a-hydroxy acid dehydrogenases 6 – Thermoanaerobacter brockii (TBADH) 1330 11a-hydroxylation of progesterone 1257 – from thermophilic organisms 1330, 1331 Index j1941 – types of 1040–1042 aldose synthesis, inverted approach for 886 – yeast alcohol dehydrogenase (YADH) 1330 aldos-2-ulose dehydratase (AUDH) 485, 486 alcohol oxidases 1346 alginate biosynthesis 594 – common oxidases 1347–1354 aliphatic a/b-unsaturated acceptor 929 – methods to diminish/avoid hydrogen aliphatic acyloins 929 peroxide 1345–1347 aliphatic alcohol oxidases 1347 alcohols, oxidation of 1325, 1408. See also aliphatic–aromatic acyloins 924–927 alcohol dehydrogenases; alcohol oxidases aliphatic donor aldehydes 925 alcoholysis of 3-arylglutaric anhydrides 339 aliphatic olefins, dihydroxylation of 1303 alcoholysis of dibenzoates 338 alkaline phosphatases 1009 aldehyde dehydrogenases 1410 – application in dephosphorylation 1012 – for biocatalytic applications 1410 – structural and mechanistic aldehyde lyases, syntheses using 993–995 description 1010, 1011 aldehyde oxidations 1392, 1407, 1409, – transphosphorylation by 1012, 1013 1414, 1416 alkaloids 770 – alcohol dehydrogenases (ADHs) 1407, alkane monooxygenases 1236, 1279, 1280, 1408 1287 – aldehyde dehydrogenases 1408–1410 alkanes 1248 – enzyme classes/applications 1392–1407 alkenal/one oxidoreductases (AORs) 1138 – with intact microbial cells 1414–1418 alkene, chemoenzymatic epoxidation of 1290 – monooxygenases 1410–1414 alkene monooxygenase 366, 1235, 1278, – oxidases 1414 1280, 1282, 1497, 1498 aldehyde reduction 1049, 1098–1101 alkene reductases, applications of 1143 – general process concept 1050 – acrylates and acrylate esters 1149 aldehydes/acids from primary alcohols – a,b-unsaturated aldehydes and – stopping oxidation at aldehyde stage ketones 1143, 1147, 1149 1363–1369 – nitroalkenes 1149, 1150 – through oxidations 1369–1373 – reductions of 2-cyclohexenones by alditol oxidase (AldO), substrate range Saccharomyces pastorianus OYE 1147 of 1355, 1356 – stereochemical investigations of old yellow aldo-keto reductases (AKRs) 1040 enzymes 1146, 1147 aldol adduct, formation of 1025 alkene reduction by whole microbial – stereo-diversity, generation 858 cells 1111, 1112 aldolases 1193 – Bakers Yeast 1112–1114 – based process 862 – microbial species 1114, 1115 – catalysis 858 alkene reductions, by isolated enzymes 1116 – catalyzed asymmetric synthesis 882 – bacterial old yellow enzyme superfamily – classes 858–861 members 1124, 1129 – class I/II aldolases, schematic – bacterial OYE homologs 1125–1128 mechanism 860 – enoate reductases 1135–1138 – nucleophilic donor substrates 859 – fungal old yellow enzyme superfamily – one-pot cascade reaction involving members 1121, 1124 with 1024 – fungal OYE homologs 1122, 1123 – reaction 866 – medium-chain dehydrogenases aldol condensation of enolate 1740 1138–1142 aldol reactions 857–909 – plant old yellow enzyme superfamily – aldolases classes 858–861 members 1129, 1130, 1135 – 2-deoxyribose 5-phosphate aldolase – plant OYE homologs 1131–1134 861–864 – Saccharomyces pastorianus old yellow – DHA/DHAP-utilizing aldolases 877–901 enzyme 1116–1121 – glycine-utilizing aldolases 901–908 – short-chain dehydrogenases 1143, 1144 – pyruvate/phosphoenolpyruvate-utilizing a-alkylated phenylserine derivatives aldolases 864–877 synthesis 908 aldose reductase 1392 2-alkyl cyclohexanones 1477 1942j Index alkyne oxyfunctionalization, type of 1314 – synthesis 661, 664 allenols 313 L-amino acid amidases 605 DL-a-allylalanine amide 608 – crystal structures 601 allyl Grignard reagents 975 amino acid amides 592 allylic alcohols 320 – dynamic kinetic resolution of 1615 allysine ethylene acetal 1192 amino acid amides, enantioselective Almac Sciences, enzyme production hydrolysis 574–618 – carbonyl reductase 1850, 1851 – enantiopure b-amino acids by – contact information 1850 b-aminopeptidases synthesis 613–618 – hydrolases 1852–1854 – enantiopure a,a-disubstituted amino acids – nitrile hydratases and nitrilases 1851 synthesis 607–613 Alzheimers disease 314 – enantiopure a-H-a-amino acids Amano