Polyamines

Polyamines are organic compounds having at least two amino groups as part of an otherwise aliphatic chain. The amino groups are usually separated by three or four methylene units, such as putrescine and spermine. Cyclen is the typical example of a class of cyclic polyamines. The polyamines are essential molecules in both eukaryotic and prokaryotic cells, and, therefore, have been isolated from all kinds of living organisms, including humans.1) Especially, the requirement for and the metabolism of polyamines are frequently dysregulated in cancer, and some polyamines can induce diseases caused by neurotoxins.2) Thus, the polyamines, which are available by chemical synthesis, have been attractive for continuing with the study of diseases.3)
This section shows the typical polyamines and the reagents used for the polyamine chemical synthesis.

Polyamines

Chemical Building Blocks for Polyamines

Reagents for Polyamine Chemical Synthesis

Polyamines

Linear Polyamines

D0239 D0239 D0081 D0081 D0108 D0108
D0099 D0099 D0090 D0090 A0310 A0310
B1814 B1814 D0493 D0493 B1468 B1468
S0068 S0068 S0385 S0385 S0069 S0069
D0239 1,4-Diaminobutane
D0081 1,4-Diaminobutane Dihydrochloride
D0108 1,5-Diaminopentane
D0099 1,5-Diaminopentane Dihydrochloride
D0090 3,3'-Diaminodipropylamine
A0310 Agmatine Sulfate
B1814 Bis(hexamethylene)triamine
D0493 Diethylenetriamine
B1468 N,N'-Bis(3-aminopropyl)-1,4-butanediamine Tetrahydrochloride
S0068 Spermidine Phosphate
S0385 Spermidine Phosphate Hexahydrate
S0069 Spermine Phosphate Hexahydrate
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Cyclic Polyamines

H1070 H1070 H1215 H1215 T1874 T1874
T1426 T1426 T1600 T1600 T1597 T1597
T1691 T1691
H1070 1,4,7,10,13,16-Hexaazacyclooctadecane
H1215 1,4,7,10,13,16-Hexaazacyclooctadecane Hexahydrochloride
T1874 1,4,7,10-Tetraazacyclododecane
T1426 1,4,7,10-Tetraazacyclododecane Tetrahydrochloride
T1600 1,4,7-Triazacyclononane Trihydrochloride
T1597 1,4,8,11-Tetraazacyclotetradecane
T1691 1,4,8,12-Tetraazacyclopentadecane
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Chemical Building Blocks for Polyamines

N-Boc-diaminoalkanes

A1371 A1371 A1372 A1372 A1373 A1373
A1374 A1374 A1375 A1375 B3052 B3052
B2810 B2810
A1371 N-(tert-Butoxycarbonyl)-1,2-diaminoethane
A1372 N-(tert-Butoxycarbonyl)-1,3-diaminopropane
A1373 N-(tert-Butoxycarbonyl)-1,4-diaminobutane
A1374 N-(tert-Butoxycarbonyl)-1,5-diaminopentane
A1375 N-(tert-Butoxycarbonyl)-1,6-diaminohexane
B3052 N-(tert-Butoxycarbonyl)-2,2-dimethyl-1,3-propanediamine
B2810 N-(tert-Butoxycarbonyl)-2-methyl-1,3-diaminopropane
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N-Cbz-diaminoalkanes

C1511 C1511 C1512 C1512 C1519 C1519
C1520 C1520 C1521 C1521
C1511 N-Carbobenzoxy-1,2-diaminoethane Hydrochloride
C1512 N-Carbobenzoxy-1,3-diaminopropane Hydrochloride
C1519 N-Carbobenzoxy-1,4-diaminobutane Hydrochloride
C1520 N-Carbobenzoxy-1,5-diaminopentane Hydrochloride
C1521 N-Carbobenzoxy-1,6-diaminohexane Hydrochloride
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N-(o-Ns)-diaminoalkanes

A2329 A2329 A1628 A1628 A2268 A2268
A1630 A1630 A1661 A1661 A1662 A1662
A2329 N-(2-Aminoethyl)-2-nitrobenzenesulfonamide Hydrochloride
A1628 N-(3-Aminopropyl)-2-nitrobenzenesulfonamide
A2268 N-(3-Aminopropyl)-2-nitrobenzenesulfonamide Hydrochloride
A1630 N-(4-Aminobutyl)-2-nitrobenzenesulfonamide
A1661 N-(5-Aminopentyl)-2-nitrobenzenesulfonamide Hydrochloride
A1662 N-(6-Aminohexyl)-2-nitrobenzenesulfonamide Hydrochloride
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Tosylamines

T1723 T1723
T1723 N,N',N''-Tris(p-toluenesulfonyl)diethylenetriamine
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Reagents for Polyamine Chemical Synthesis

N-Protecting Agents

B1969 B1969 D1463 D1463 B0988 B0988
B1089 B1089 N0142 N0142 N0363 N0363
F0197 F0197 B3021 B3021 C0176 C0176
C1591 C1591 C1574 C1574 D1547 D1547
D3878 D3878 D3879 D3879 D3880 D3880
P1277 P1277 P1281 P1281 C1131 C1131
C1124 C1124 C0683 C0683 B0916 B0916
F0239 F0239 C0933 C0933
B1969 1-tert-Butoxycarbonyl-1,2,4-triazole
D1463 2,4-Dinitrophenylsulfenyl Chloride
B0988 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
B1089 2-(tert-Butoxycarbonylthio)-4,6-dimethylpyrimidine [Boc Agent for Peptides Synthesis]
N0142 2-Nitrobenzenesulfonyl Chloride
N0363 2-Nitrophenylsulfenyl Chloride [N-Protecting Agent for Peptides Research]
F0197 9-Fluorenylmethyl Chloroformate [N-Protecting Agent for Peptides Research]
B3021 Benzyl Chloroformate
C0176 Benzyl Chloroformate (30-35% in Toluene)
C1591 Carbonic Acid Benzyl 4-Nitrophenyl Ester
C1574 Carbonic Acid tert-Butyl 2,4,5-Trichlorophenyl Ester
D1547 Di-tert-butyl Dicarbonate [Boc-reagent for Amino Acid]
D3878 Di-tert-butyl Dicarbonate (ca. 30% in Dioxane)
D3879 Di-tert-butyl Dicarbonate (ca. 30% in Tetrahydrofuran)
D3880 Di-tert-butyl Dicarbonate (ca. 30% in Toluene)
P1277 Diallyl Pyrocarbonate
P1281 Dibenzyl Pyrocarbonate
C1131 N-(2-Chlorobenzyloxycarbonyloxy)succinimide
C1124 N-Carbobenzoxyoxysuccinimide
C0683 N-Ethoxycarbonylphthalimide [for Peptide Synthesis]
B0916 N-tert-Butoxycarbonylimidazole
F0239 N-[(9H-Fluoren-9-ylmethoxy)carbonyloxy]succinimide
C0933 tert-Butyl Carbazate
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Amination

A1137 A1137 A1441 A1441 I0497 I0497
B1734 B1734 D2361 D2361 D1672 D1672
M1182 M1182 H0093 H0093 H0258 H0258
H0196 H0196 H0530 H0530 D1899 D1899
B2303 B2303 B1648 B1648 A1632 A1632
C1757 C1757 M0343 M0343 M0886 M0886
P1235 P1235 P0403 P0403 D2479 D2479
I0510 I0510 B2857 B2857 T1184 T1184
A1137 4-Amino-1,2,4-triazole
A1441 Acetoxime O-(2,4,6-Trimethylphenylsulfonate)
I0497 Di-tert-butyl Iminodicarboxylate
B1734 Diethyl N-(tert-Butoxycarbonyl)phosphoramidate
D2361 Diethyl Phosphoramidate
D1672 Diphenylphosphoryl Azide
M1182 Ethyl O-Mesitylsulfonylacetohydroxamate [Precursor of the Powerful Aminating Reagent]
H0093 Hexamethylenetetramine
H0258 Hydroxylamine Hydrochloride
H0196 Hydroxylamine Sulfate
H0530 Hydroxylamine-O-sulfonic Acid
D1899 N,O-Dimethylhydroxylamine Hydrochloride
B2303 N-(tert-Butoxycarbonyl)-2-nitrobenzenesulfonamide
B1648 N-(tert-Butoxycarbonyl)-p-toluenesulfonamide
A1632 N-Allyloxycarbonyl-2-nitrobenzenesulfonamide
C1757 N-Carbobenzoxy-2-nitrobenzenesulfonamide
M0343 O-Methylhydroxylamine Hydrochloride
M0886 O-Methylhydroxylamine Hydrochloride (ca. 40% in Water, ca. 5.4mol/L)
P1235 Phthalimide DBU Salt
P0403 Phthalimide Potassium Salt
D2479 Sodium Diformylamide
I0510 tert-Butyl Methyl Iminodicarboxylate
B2857 tert-Butyl [Bis(4-methoxyphenyl)phosphinyloxy]carbamate
T1184 Trimethylsilylmethyl Azide
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Literature

1) S. Bienz, P. Bisegger, A. Guggisberg, M. Hesse, Nat. Prod. Rep. 2005, 22, 647 (Review) [DOI]; C. Wang, J.-G. Delcros, L. Cannon, F. Konate. H. Carias, J. Biggerstaff, R. A. Gardner, O. Phanstiel IV, J. Med. Chem. 2003, 46, 5129 [DOI].
2) E. W. Gerner, F. L. Meyskens Jr, Nat. Rev. Cancer 2004, 4, 781 [DOI]; R. A. Casero Jr, L. J. Marton, Nat. Rev. Drug Discov. 2007, 6, 373.
3) T. Fukuyama, M. Cheung, T. Kan, Synlett 1999, 1301 [DOI]; T. Kan, A. Fujiwara, H. Kobayashi, T. Fukuyama, Tetrahedron 2002, 58, 6267 [DOI]; Y. Hidai, T. Kan, T. Fukuyama, Tetrahedron Lett. 1999, 40, 4711 [DOI]; Y. Hidai, T. Kan, T. Fukuyama, Chem. Pharm. Bull. 2000, 48, 1570; T. Kan, A. Fujiwara, H. Kobayashi, T. Fukuyama, Tetrahedron 2002, 58, 6267 [DOI]; M. Matoba, T. Kajimoto, M. Node, Synth. Commun. 2008, 38, 1194 [DOI].


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