- Peptide Synthesis
/ M. Bodanszky; Y. S. Klausner; M. A. Ondetti.
- 2. Edition
- New York (etc.) : John Wiley & Sons, 1976.
- xiv,208p.
- ISBN 0-471-08451-4.
Nyelv(ek):angol
Tartalom:
-Peptidek szintézise
-szerves kémia, peptidek, szintézis,
védőcsoportok, racemizáció, szilárd
fázisú peptidszintézis (SPPS)
-kémia
-(35 fejezet)
Fejezetek:
*Part-1:Introduction,
etc. (3 chapters) (1-13 p.)
*Introduction:
References, Proceedings of the European Peptide Symposia, Proceedings of
the American Peptide Symposia, Monographs on peptide synthesis, Selected
review articles on peptide synthesis (1-5 p.)
*Historical
aspects and perspectives: Toward biologically active peptides, Synthetic
methods, New techniques, References (5-10 p.)
*Problems
of peptide synthesis: Coupling, Protecting groups, Racemization, Strategy
and techniques, References (10-13 p.)
*Part-2:Easily
removable protecting groups and their removal (10 chapters) (13-85 p.)
*Protection
of amino groups: Amine hydrochlorides, The p-toluenesulfonyl group, The
benzyloxycarbonyl (carbobenzoxy) group, Substituted benzyloxycarbonyl and
other urethane-type protecting groups, The t-butyloxycarbonyl group, Thiourethane-type
derivatives, The trifluoroacetyl group, The chloroacetyl group, The phthalyl
group, The formyl group, The acetoacetyl group, The 4,5-diphenyl-4-oxazolin-2-one
(ox) group, the benzyl/diphenylinethyl (benzhydryl) and triphenylmethyl
(trityl) groups, Lactams, Schiff bases and enamines, Tritylsulfenyl and
arylsulfenyl groups) (13-49 p.)
*Protection
of carboxyl groups: Salt formation, Methyl and ethyl esters, Benzyl and
benzhydryl esters, Substituted benzyl esters, Phthalimidomethyl esters,
Tertiary butyl esters, Phenacyl esters, Phenyl esters, 4-Picolyl esters,
2-Methylthioethyl/2(p-toluenesulfonyl)ethyl and 2(p-nitrothiophenyl)ethyl
esters, p-Methylthiophenyl esters, Hydrazides, Selective protection of
carboxyl groups of monoaminodicarboxylicacids (49-58 p.)
*Protection
of hydroxyl groups: O-Acyl derivatives, O-Alkyl derivatives (58-60 p.)
*Protection
of sulfhydryl groups (60-61 p.)
*Protection
of the imidazole nitrogen of histidine: N-im-Benzylhistidine, N-im-Tritylhistidine,
N-im-Benzyloxycarbonylhistidine, N-im-t-Butyloxycarbonylhistidine, N-im-Adamantyloxycarbonylhistidine,
N-im-Piperidinocarbonylhistidine, N-im-2,4-Dinitrophenylhistidine (61-67
p.)
*Protection
of the guanidino group of arginine (67-68 p.)
*Protection
of amide side chains (68-69 p.)
*Protection
of the thio ether group in methionine: (69 p.)
*Protection
of the indole ring in tryptophan (69 p.)
*References
(69-85 p.)
*Part-3:Formation
of the peptide bond (6 chapters) (85-137 p.)
*Reactive
derivatives of the carboxyl component: The azide method, The acid chloride
method, The acid anhydride methods, Activated and active esters (85-109
p.)
*Reactive
derivatives of the amino component (109-111 p.)
*Reactive
N-acyl derivatives (111-114 p.)
*Coupling
reagents: Carbodiimides, Isoxazolium derivatives, EEDQ, Phosphonium derivatives
(114-125 p.)
*Nonconventional
methods of coupling (125-128 p.)
*References
(128-137 p.)
*Part-4:Racemization
(7 chapters) (137-158 p.)
*Mechanisms
of racemization (137-143 p.)
*Racemization
during introduction and removal of protecting groups (143-144 p.)
*Racemization
during peptide bond formation: Influence of the amino protecting group,
Influence of the coupling methods, Influence of the individual amino acids
(144-149 p.)
*Methods
for the study of racemization (149-150 p.)
*Examination
of the optical purity of synthetic peptides (150-151 p.)
*Prevention
of racemization (151-153 p.)
*References.(153-158
p.)
*Part-5:Solid
phase peptide synthesis and other techniques for the facilitation of synthetic
procedures (4 chapters) (158-177 p.)
*Solid phase
peptide synthesis (SPPS): The polymeric support, The bond between peptide
chain and polymer, Alpha-amino protecting groups and their removal in SPPS,
Side chain protection in SPPS, Formation of the peptide bond in SPPS, Racemizaiton
in SPPS, Cleavage of the completed peptide chain from the polymeric support,
Mechanization/automation and monitoring in SPPS (158-169 p.)
*Polymer-bound
reagents (169-170 p.)
*Facilitation
of synthesis in solution: Isolation of intermediates with the aid of polymers,
Synthesis of peptide chains without isolation of intermediates, "In situ"
peptide synthesis (172-173 p.)
*References
(173-177 p.)
*Part-6:Strategy
and tactics of peptide synthesis (5 chapters) (177-197 p.)
*Strategy:
Stepwise elongation from the N-terminal amino acid, Stepwise elongation
from the C-terminal amino acid, Fragment condensation (177-182 p.)
*Tactics
in the selection of protecting groups and coupling methods (182-187 p.)
*Special
problems: Disulfide bonds, Cyclic peptides (187-192 p.)
*Purification
of intermediates and final products in peptide synthesis (192 p.)
*References
(192-197 p.) |