684
INDEX
FMN and FAD, in oxidation–reduction
sequences 456
Folic acid (vitamin B 9 )
biosynthesis 275
structure 453
Folinic acid, structure 455
Formal charge
ammonium cation 47
calculation 46
common atoms and ions 47
hydronium cation 47
methyl anion 47
in mechanisms168
Formaldehyde
bonding molecular orbitals 35
hydrate (formalin) 234
resonance structures 49
Forosamine, in spiramycin 494
Free energy, see standard free energy
Free radical, see radical
Friedel–Crafts reactions
acylations 308
in synthesis of ibuprofen 314
intramolecular acylations 309
alkylations 306–8
rearrangement reactions in 217, 307
carbocations in 306
Lewis acids in 306
Frost circle 43
benzene 43
cyclooctatetraene 43
pyridine 406
pyrrole 406
Fructofuranose 469
Fructopyranose 469
Fructose
fructofuranose forms 469
fructopyranose forms 469
hemiketal form, structure 471
in invert sugar 231
from isomerization of glucose 467
structure and stereochemistry 464
Fructose 1,6-diphosphate, in glycolysis 580
Fructose 6-phosphate
in glycolysis 579
tautomerism 350
Fucose, in blood group antigens 496
Fumarase, in Krebs cycle 589
Fumarate, in Krebs cycle 588
Functional groups 2, 4, Table 5–6
inductive effects, Table 126
resonance effects, Table 134
Functional group transformations, of aromatic
substituents 315
Furan
dipole 427
molecular structure 426
resonance structures 426
and thiophene, reactivity 427
Furanose
forms 468
ring 227
Furanose and pyranose forms, aldohexoses,
equilibrium proportions, Table 470
Furosemide (frusemide) 275
Fused ring systems, stereochemistry 107–16
Fused rings, aromaticity 44
GABA (γ-aminobutyric acid)
from glutamic acid 602
transamination 602
Galactosamine, structure 492
Galactose
in blood group antigens 496
Fischer projection 104
hemiacetal form, structure 471
structure and stereochemistry 465
β-Galactosidase 476
Galacturonic acid
in heparin 496
in pectins 488
synthesis 487
Garosamine, in gentamicin 494
Gases, noble 19
gauche
conformer 59
interaction, substituted cyclohexanes
67
gem
definition 234
diacids, decarboxylation 390
diols 234
Gene, definition 555
General acid catalyst, definition 434, 517
General base catalyst, definition 434, 517
Genetic code 555
mRNA sequences, Table 555
Gentamicin C 1 , structure 494
Geometric isomers, definition 83
Geranyl diphosphate
allylic cation 197
in terpenoid and steroid biosynthesis 301
Geranylgeranyl diphosphate, in terpenoid
biosynthesis 301
Glucaric acid
lactones 486
structure 486
Glucitol, structure 473
Glucocorticoids, function 291
Glucofuranose 468
Glucofuranoside, structure 474
Gluconic acid, structure 486
Glucopyranose 226, 468
anomeric forms 226
Glucopyranoside, structure 474
Glucoraphanin, structure 477
Glucosamine,
biosynthesis 492
in chitin 495
structure 492
synthesis 492
Glucose
blood, see blood glucose
cyclic hemiacetal, conformation 72
degradation in glycolysis 579
energy yield 584, 589, 592
enolization 467
Fischer projection 104
glucofuranose form 468
glucopyranose form 468
hemiacetal form 226, 468, 471
from Fischer projection 105
structure 471
in invert sugar 231
isomerization 467
14 C-labelled, synthesis 465
mutarotation 226
structure and stereochemistry 464, 465
Glucose oxidase, in monitoring of blood
glucose 486
Glucose 6-phosphate
in glycolysis 579
tautomerism 350
β-Glucosidase 476
α-1,6-Glucosidase 485
Glucosinolates, definition 477
Glucuronic acid
in glycyrrhizin 488
synthesis 487
in vitamin C biosynthesis 490
Glucuronides, in drug metabolism 489
Glutamate dehydrogenase 598
Glutamate transaminase 599
Glutamic acid
ionization 502
at pH 7 152
isoelectric point, calculation 161
from reductive amination 598
structure and pK a values 500
Glutamine
as amide 261
structure and pK a values 500
Glutaric acid, acidity 144
Glutathione
conjugates 201, 203, 399
paracetamol 400
dimer 508
formation of disulfide bridge 508
structural abbreviation 505
structure 505, 508
as sulfur nucleophile 201, 203, 399
Glutathione peroxidase 508
Glutathione reductase 508
Glutathione S-transferases 201
Glyceraldehyde, D and L configurations 103
Glyceraldehyde 3-phosphate
from glycerol 590
in glycolysis 581
tautomerism 350
Glyceraldehyde 3-phosphate dehydrogenase,
in glycolysis 581
Glycerol, in hydrolysis of fats 590
Glycine, structure and pK a values 500
Glycogen
as polyacetal 232
structure 484
Glycolysis 579–84
aldol reactions 363
aldolase active site 526
aldolase mechanism 525
energy yield 584
enols and enolization 350
triose phosphate isomerase mechanism 524
Glycolytic pathway, see glycolysis
Glycoproteins, as blood group antigens 496
Glycosaminoglycan, definition 496
Glycosides
conformational isomerism 475
cyanogenic, definition 477
definition 474
equilibration of anomers 475
C-glycosides, natural 476
N-glycosides, natural 476
O-glycosides, natural 476
INDEX
FMN and FAD, in oxidation–reduction
sequences 456
Folic acid (vitamin B 9 )
biosynthesis 275
structure 453
Folinic acid, structure 455
Formal charge
ammonium cation 47
calculation 46
common atoms and ions 47
hydronium cation 47
methyl anion 47
in mechanisms168
Formaldehyde
bonding molecular orbitals 35
hydrate (formalin) 234
resonance structures 49
Forosamine, in spiramycin 494
Free energy, see standard free energy
Free radical, see radical
Friedel–Crafts reactions
acylations 308
in synthesis of ibuprofen 314
intramolecular acylations 309
alkylations 306–8
rearrangement reactions in 217, 307
carbocations in 306
Lewis acids in 306
Frost circle 43
benzene 43
cyclooctatetraene 43
pyridine 406
pyrrole 406
Fructofuranose 469
Fructopyranose 469
Fructose
fructofuranose forms 469
fructopyranose forms 469
hemiketal form, structure 471
in invert sugar 231
from isomerization of glucose 467
structure and stereochemistry 464
Fructose 1,6-diphosphate, in glycolysis 580
Fructose 6-phosphate
in glycolysis 579
tautomerism 350
Fucose, in blood group antigens 496
Fumarase, in Krebs cycle 589
Fumarate, in Krebs cycle 588
Functional groups 2, 4, Table 5–6
inductive effects, Table 126
resonance effects, Table 134
Functional group transformations, of aromatic
substituents 315
Furan
dipole 427
molecular structure 426
resonance structures 426
and thiophene, reactivity 427
Furanose
forms 468
ring 227
Furanose and pyranose forms, aldohexoses,
equilibrium proportions, Table 470
Furosemide (frusemide) 275
Fused ring systems, stereochemistry 107–16
Fused rings, aromaticity 44
GABA (γ-aminobutyric acid)
from glutamic acid 602
transamination 602
Galactosamine, structure 492
Galactose
in blood group antigens 496
Fischer projection 104
hemiacetal form, structure 471
structure and stereochemistry 465
β-Galactosidase 476
Galacturonic acid
in heparin 496
in pectins 488
synthesis 487
Garosamine, in gentamicin 494
Gases, noble 19
gauche
conformer 59
interaction, substituted cyclohexanes
67
gem
definition 234
diacids, decarboxylation 390
diols 234
Gene, definition 555
General acid catalyst, definition 434, 517
General base catalyst, definition 434, 517
Genetic code 555
mRNA sequences, Table 555
Gentamicin C 1 , structure 494
Geometric isomers, definition 83
Geranyl diphosphate
allylic cation 197
in terpenoid and steroid biosynthesis 301
Geranylgeranyl diphosphate, in terpenoid
biosynthesis 301
Glucaric acid
lactones 486
structure 486
Glucitol, structure 473
Glucocorticoids, function 291
Glucofuranose 468
Glucofuranoside, structure 474
Gluconic acid, structure 486
Glucopyranose 226, 468
anomeric forms 226
Glucopyranoside, structure 474
Glucoraphanin, structure 477
Glucosamine,
biosynthesis 492
in chitin 495
structure 492
synthesis 492
Glucose
blood, see blood glucose
cyclic hemiacetal, conformation 72
degradation in glycolysis 579
energy yield 584, 589, 592
enolization 467
Fischer projection 104
glucofuranose form 468
glucopyranose form 468
hemiacetal form 226, 468, 471
from Fischer projection 105
structure 471
in invert sugar 231
isomerization 467
14 C-labelled, synthesis 465
mutarotation 226
structure and stereochemistry 464, 465
Glucose oxidase, in monitoring of blood
glucose 486
Glucose 6-phosphate
in glycolysis 579
tautomerism 350
β-Glucosidase 476
α-1,6-Glucosidase 485
Glucosinolates, definition 477
Glucuronic acid
in glycyrrhizin 488
synthesis 487
in vitamin C biosynthesis 490
Glucuronides, in drug metabolism 489
Glutamate dehydrogenase 598
Glutamate transaminase 599
Glutamic acid
ionization 502
at pH 7 152
isoelectric point, calculation 161
from reductive amination 598
structure and pK a values 500
Glutamine
as amide 261
structure and pK a values 500
Glutaric acid, acidity 144
Glutathione
conjugates 201, 203, 399
paracetamol 400
dimer 508
formation of disulfide bridge 508
structural abbreviation 505
structure 505, 508
as sulfur nucleophile 201, 203, 399
Glutathione peroxidase 508
Glutathione reductase 508
Glutathione S-transferases 201
Glyceraldehyde, D and L configurations 103
Glyceraldehyde 3-phosphate
from glycerol 590
in glycolysis 581
tautomerism 350
Glyceraldehyde 3-phosphate dehydrogenase,
in glycolysis 581
Glycerol, in hydrolysis of fats 590
Glycine, structure and pK a values 500
Glycogen
as polyacetal 232
structure 484
Glycolysis 579–84
aldol reactions 363
aldolase active site 526
aldolase mechanism 525
energy yield 584
enols and enolization 350
triose phosphate isomerase mechanism 524
Glycolytic pathway, see glycolysis
Glycoproteins, as blood group antigens 496
Glycosaminoglycan, definition 496
Glycosides
conformational isomerism 475
cyanogenic, definition 477
definition 474
equilibration of anomers 475
C-glycosides, natural 476
N-glycosides, natural 476
O-glycosides, natural 476