Crystal and molecular structure of <scp>L</scp>-cystine dimethyl ester dihydrochloride monohydrate

Vijayalakshmi, B.; Srinivasan, R.

doi:10.1107/s0567740875004360

Cited by 7 publications

(1 citation statement)

References 15 publications

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“…These interactions occur in crystalline cystine and selenocystine, two naturally occurring amino acids (Figure ). , The biological relevance of these compounds and of some others discussed above (Figure ) suggests that the ChB donor ability of the moieties discussed in this paragraph may have a nonminor biological importance. Dicyanodiselenide functions as a tetradentate ChB donor consistent with the computed presence of two σ-holes on any selenium atom (Figure ).…”

Section: Sulfides Disulfides and Selenium And Tellurium Analoguesmentioning

confidence: 99%

The Chalcogen Bond in Crystalline Solids: A World Parallel to Halogen Bond

2019

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Conspectus The distribution of the electron density around covalently bonded atoms is anisotropic, and this determines the presence, on atoms surface, of areas of higher and lower electron density where the electrostatic potential is frequently negative and positive, respectively. The ability of positive areas on atoms to form attractive interactions with electron rich sites became recently the subject of a flurry of papers. The halogen bond (HaB), the attractive interaction formed by halogens with nucleophiles, emerged as a quite common and dependable tool for controlling phenomena as diverse as the binding of small molecules to proteinaceous targets or the organization of molecular functional materials. The mindset developed in relation to the halogen bond prompted the interest in the tendency of elements of groups 13–16 of the periodic table to form analogous attractive interactions with nucleophiles. This Account addresses the chalcogen bond (ChB), the attractive interaction formed by group 16 elements with nucleophiles, by adopting a crystallographic point of view. Structures of organic derivatives are considered where chalcogen atoms form close contacts with nucleophiles in the geometry typical for chalcogen bonds. It is shown how sulfur, selenium, and tellurium can all form chalcogen bonds, the tendency to give rise to close contacts with nucleophiles increasing with the polarizability of the element. Also oxygen, when conveniently substituted, can form ChBs in crystalline solids. Chalcogen bonds can be strong enough to allow for the interaction to function as an effective and robust tool in crystal engineering. It is presented how chalcogen containing heteroaromatics, sulfides, disulfides, and selenium and tellurium analogues as well as some other molecular moieties can afford dependable chalcogen bond based supramolecular synthons. Particular attention is given to chalcogen containing azoles and their derivatives due to the relevance of these moieties in biosystems and molecular materials. It is shown how the interaction pattern around electrophilic chalcogen atoms frequently recalls the pattern around analogous halogen, pnictogen, and tetrel derivatives. For instance, directionalities of chalcogen bonds around sulfur and selenium in some thiazolium and selenazolium derivatives are similar to directionalities of halogen bonds around bromine and iodine in bromonium and iodonium compounds. This gives experimental evidence that similarities in the anisotropic distribution of the electron density in covalently bonded atoms translates in similarities in their recognition and self-assembly behavior. For instance, the analogies in interaction patterns of carbonitrile substituted elements of groups 17, 16, 15, and 14 will be presented. While the extensive experimental and theoretical data available in the literature prove that HaB and ChB form twin supramolecular synthons in the solid, more experimental information has to become available before such a statement can be safely extended to interactions wherein ele...

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Section: Sulfides Disulfides and Selenium And Tellurium Analoguesmentioning

confidence: 99%

The Chalcogen Bond in Crystalline Solids: A World Parallel to Halogen Bond

2019

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Helix‐coil stability constants for the naturally occurring amino acids in water. XXIV. Half‐cystine parameters from random poly(hydroxybutylglutamine‐CO‐S‐methylthio‐L‐cysteine)

1990

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SYNOPSISWater-soluble, random copolymers containing N 5-(4-hydroxybutyl ) -L-glutamine (host) and S-methylthio-L-cysteine (guest) have been prepared, fractionated, and characterized, with S-methylthio-L-cysteine serving as a model for cystine residues in proteins. From the thermally induced helix-coil transition curves of these copolymers in water a t neutral pH, the Zimm-Bragg parameters CJ and s for the helix-coil transition of "poly (L-cystine)" were deduced. The results show that the cystine model acts as a weak helix-breaker over the entire temperature range from 0 to 60°C. The implications of this finding are evaluated in the context of a general discussion of the Zimm-Rragg parameters for all the 20 naturally occurring amino acids

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X-Ray Crystal Structures of Amino Acids and Selected Derivatives

Cody¹

1985

Chemistry and Biochemistry of the Amino Acids

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Crystal and molecular structure of L-cystine dimethyl ester dihydrochloride monohydrate

Cited by 7 publications

References 15 publications

The Chalcogen Bond in Crystalline Solids: A World Parallel to Halogen Bond

The Chalcogen Bond in Crystalline Solids: A World Parallel to Halogen Bond

Helix‐coil stability constants for the naturally occurring amino acids in water. XXIV. Half‐cystine parameters from random poly(hydroxybutylglutamine‐CO‐S‐methylthio‐L‐cysteine)

X-Ray Crystal Structures of Amino Acids and Selected Derivatives

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