x
CONTENTS
11.10.3 Bischler–Napieralski isoquinoline synthesis
459
11.10.4 Pictet–Spengler tetrahydroisoquinoline synthesis
460
11.10.5 Knorr pyrrole synthesis
460
11.10.6 Paal–Knorr pyrrole synthesis
461
11.10.7 Fischer indole synthesis
461
12 Carbohydrates
463
12.1 Carbohydrates
463
12.2 Monosaccharides
463
12.2.1
Enolization and isomerization
467
12.2.2
Cyclic hemiacetals and hemiketals
468
12.2.3
The anomeric centre
469
12.3 Alditols
473
12.4 Glycosides
474
12.5 Cyclic acetals and ketals: protecting groups
481
12.6 Oligosaccharides
482
12.7 Polysaccharides
484
12.7.1
Structural aspects
484
12.7.2
Hydrolysis of polysaccharides
485
12.8 Oxidation of sugars: uronic acids
485
12.9 Aminosugars
492
12.10 Polymers containing aminosugars
495
13 Amino acids, peptides and proteins
499
13.1 Amino acids
499
13.2 Peptides and proteins
504
13.3 Molecular shape of proteins: primary, secondary and tertiary structures
505
13.3.1
Tertiary structure: intramolecular interactions
511
13.3.2
Protein binding sites
513
13.4 The chemistry of enzyme action
515
13.4.1
Acid–base catalysis
516
13.4.2
Enolization and enolate anion biochemistry
523
13.4.3
Thioesters as intermediates
530
13.4.4
Enzyme inhibitors
530
13.5 Peptide biosynthesis
533
13.5.1
Ribosomal peptide biosynthesis
533
13.5.2
Non-ribosomal peptide biosynthesis
535
13.6 Peptide synthesis
540
13.6.1
Protecting groups
540
13.6.2
The dicyclohexylcarbodiimide coupling reaction
542
13.6.3
Peptide synthesis on polymeric supports
542
13.7 Determination of peptide sequence
544
14 Nucleosides, nucleotides and nucleic acids
549
14.1 Nucleosides and nucleotides
549
14.2 Nucleic acids
551
14.2.1
DNA
551
14.2.2
Replication of DNA
553
14.2.3
RNA
555