NDLI: Salts of Tryptophan with p-Toluenesulphonic Acid and Camphorsulphonic Acids

Content Provider	Springer Nature Link
Author	Sayed, Amina Jacobs, Ayesha
Copyright Year	2015
Abstract	Co-crystallisation of dl-tryptophan with p-toluenesulphonic acid, R-camphor-10-sulphonic acid and S-camphor-10-sulphonic acid resulted in salts. For all the structures, the amino acid is in the cationic form with the proton transferred from the acidic co-former to the amino acid. R-camphor-10-sulphonic acid and S-camphor-10-sulphonic acid were unsuccessful at resolving dl-tryptophan. Dissolution of the respective camphorsulphonic acid and dl-tryptophan in methanol/water gave crystals which contained equimolar amounts of the d- and the l-tryptophan. The following salts were also obtained in aqueous acetonitrile; (2l-TRP$^{+}$)(2S-CSA$^{−}$)·(H$_{2}$O) from a mixture of l-TRP/S-CSA and (d-TRP$^{+}$)(S-CSA$^{−}$) from a mixture of d-TRP/S-CSA. The crystal structures and the thermal stability of the salts have been determined. (dl-TRP$^{+}$)(p-TSA$^{−}$) solved in P2$_{1}$/c with a = 19.422(2) Å, b = 5.5456(7) Å, c = 16.488(2) Å and β = 102.357(2)°. (d-TRP$^{+}$)(l-TRP$^{+}$)(2R-CSA$^{−}$) solved in P2$_{1}$ with a = 12.780(3) Å, b = 10.411(2) Å, c = 32.574(7) Å and β = 97.60(3)°. (d-TRP$^{+}$)(l-TRP$^{+}$)(2S-CSA$^{−}$) solved in P2$_{1}$ with a = 12.783(3) Å, b = 10.410(2) Å, c = 32.564(7) Å and β = 97.44(3)°. (2l-TRP$^{+}$)(2S-CSA$^{−}$)·(H$_{2}$O) solved in P2$_{1}$ with a = 13.1761(12) Å, b = 10.3092(10) Å, c = 16.6268(16) Å and β = 104.435(2)°. (d-TRP$^{+}$)(S-CSA$^{−}$) solved in P2$_{1}$2$_{1}$2$_{1}$ with a = 6.4185(13) Å, b = 12.700(3) Å, c = 25.173(5) Å and α = β = γ = 90°. dl-tryptophan forms salts with p-toluenesulphonic acid, R-camphor-10-sulphonic acid and S-camphor-10-sulphonic acid. l-tryptophan forms a salt hydrate with S-camphor-10-sulphonic acid and d-tryptophan forms a salt with S-camphor-10-sulphonic acid. The crystal structures and the thermal stability of the salts are reported.
Starting Page	57
Ending Page	66
Page Count	10
File Format	PDF
ISSN	10741542
Journal	Journal of Chemical Crystallography
Volume Number	46
Issue Number	2
e-ISSN	15728854
Language	English
Publisher	Springer US
Publisher Date	2015-12-07
Publisher Place	New York
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Tryptophan Camphorsulphonic acids p-Toluenesulphonic acid Chiral resolution Amino acid Organometallic Chemistry Crystallography Physical Chemistry Inorganic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics

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