A neutron diffraction study of <scp>L</scp>-cysteine

Kerr, K. Ann; Ashmore, Jason; Koetzle, T. F.

doi:10.1107/s0567740875006772

Cited by 115 publications

(118 citation statements)

References 4 publications

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“…7) At the same time no influence of the bulky S-trityl group on the S-C(Cys) distance is observed; the S1-C2 bond of 1.811 (5) Å has a similar length to that in the native L-cysteine molecules (1.798-1.819 Å). 20,21) The Boc moiety of Boc-Cys(Trt)-OtBu has average bond lengths (Table 2) and the common trans conformation in agreement with the literature 2,4) and our CSD search (164 Boc derivatives, of which 158 is trans, including four, also trans, Boc-Cys fragment 22) ). The OtBu moiety of BocCys(Trt)-OtBu has a rigid geometry (the analysis of 87 tertbutyl ester fragments, none of which was Cys-OtBu).…”

Section: Resultssupporting

confidence: 63%

The Molecular and Crystal Structure of tert-Butyl N.ALPHA.-tert-Butoxycarbonyl-L-(S-trityl)cysteinate and the Conformation-Stabilizing Function of Weak Intermolecular Bonding.

Kozioł

Szady

Masiukiewicz

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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The title compound, C 31 H 37 NO 4 S {systematic name: (R)-tert-butyl-2-[(tert-butoxycarbonyl)amino]-3-(tritylsulfanyl)propanoate} is an L-cysteine derivative with three functions: NH 2 , COOH and SH, blocked by protecting groups tert-butoxycarbonyl, tert-butyl and trityl, respectively. The main chain of the molecule adopts the extended, nearly all-trans C 5 conformation with the intramolecular N-H· · · O‫؍‬C hydrogen bond. The urethane group is not involved in any intermolecular hydrogen bonding. Only weak intermolecular hydrogen bonds and hydrophobic contacts are observed in the crystal structure. These are C-H· · ·O hydrogen bonds and CH/p p interactions with donor· · ·acceptor distances, C· · ·O ca. 3.5 Å and C· · ·C ca. 3.7 Å, respectively. The first type of interaction links phenyl H-atoms and carbonyl groups. The second type of interaction is formed between a methyl group of the tert-butyl fragment and a trityl phenyl ring. The resulting molecular conformation in the crystal is very close to an ab initio minimum energy conformer of the isolated molecule. The extended C 5 conformation of the main peptide chain is the same and there is slight discrepancy in the disposition of trityl phenyl rings. Their small dislocation creates the possibility of forming the entire network above of extensive, specific, weak intermolecular interactions; these constrain the molecule and permit it to retain the minimum energy C 5 conformation of its main chain in the solid state. In contrast, in n-hexane solution, where such specific interactions cannot occur, only a small population of the molecules adopts the extended C 5 conformation.

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Section: Resultssupporting

confidence: 63%

The Molecular and Crystal Structure of tert-Butyl N.ALPHA.-tert-Butoxycarbonyl-L-(S-trityl)cysteinate and the Conformation-Stabilizing Function of Weak Intermolecular Bonding.

Kozioł

Szady

Masiukiewicz

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…L-Cysteine crystallizes in the monoclinic and orthorhombic forms and has been structurally characterized by X-ray [8][9][10] and neutron [11] diffraction methods at ambient and low temperatures [12][13][14] as well as at ambient and higher pressures [15]. Phase transitions have been detected when lowering the temperature (ca.…”

Section: Introductionmentioning

confidence: 99%

“…Structural data for the polymorphic forms of L-cysteine and L-cystine was obtained from the Cambridge Structural Database [32] (CSD refcodes: LCYSTN to LCYSTN36 for L-cysteine [8][9][10][11][12][13][14][15] and LCYSTI10 to LCYSTI13 for L-cystine [16][17][18][19]). The PLATON [33] (as incorporated into the WinGX package [34]) and XPowder [35] software were used to prepare material for visualization and analysis.…”

Section: X-ray Diffraction Studiesmentioning

confidence: 99%

Thermal behavior and polymorphism in medium–high temperature range of the sulfur containing amino acids l-cysteine and l-cystine

Foces‐Foces

Roux

Notario

et al. 2011

J Therm Anal Calorim

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A thermophysical study of the sulfur containing amino acids L-cysteine and L-cystine has been carried out by differential scanning calorimetry (DSC). Heat capacities of both compounds were measured in the temperature interval from T = 268 K to near their respective melting temperatures. DSC and variable temperature powder X-ray diffraction analysis (PXRD) gave evidence for a solid-solid phase transition close to the melting point only in the L-cysteine sample. DSC experiments show that this solidsolid transition is not reversible in the temperature interval T = 235-485 K and presents a behavior depending on heating temperature, time, and rate. This behavior is also supported by variable-temperature PXRD. The patterns for the commercial samples, at room temperature, are consistent with those simulated for the orthorhombic and hexagonal polymorphic forms from the single-crystal X-ray analysis.

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“…L-serine has a framework crystal structure [83,84] similar to those of L-alanine [58][59][60][61][62], DL-alanine [57,58], or the orthorhombic polymorph of L-cysteine [66,67], and its side chain, CH 2 OH, is involved in the formation of intermolecular OH … O hydrogen bonds which are stronger than the SH … O or SH… S bonds. At ambient pressure, OH … O hydrogen bonds are formed between the -CH 2 OH groups of the neighbouring chains of molecules.…”

Section: Structure Stabilization By the Second Componentmentioning

confidence: 99%

“…In the crystals of L-and DL-cysteine, the side chains -CH 2 SH can form weak hydrogen bonds either with the side chains of the neighbouring molecules (SH … S) or with the terminal carboxy-groups (SH … O) [66][67][68][69]. The crystals of the orthorhombic polymorph of L-cysteine show several phase transitions at pressures between 1 GPa and at 3.9 GPa, and these transitions are related to the rotation of the side chains and the formation of new types of hydrogen bonds [70,71].…”

Section: Structure Stabilization By the Second Componentmentioning

confidence: 99%

Multicomponent organic crystals at high pressure

Boldyreva

2014

Zeitschrift Für Kristallographie Crystalline Materials

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High-pressure research of the crystals of organic and coordination compounds is now a well-established field. However, the studies of multicomponent crystals (hydrates, solvates, salts and co-crystals) are just emerging. The aim of this paper is to give a personal view of what makes the multicomponent organic systems peculiar for high-pressure research as compared with the monocomponent ones. Several different types of structure response to compression and reverse decompression are reviewed with examples based on research of salts, co-crystals and hydrates of amino acids. Challenges and prospects of further studies are discussed.

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A neutron diffraction study of L-cysteine

Cited by 115 publications

References 4 publications

The Molecular and Crystal Structure of tert-Butyl N.ALPHA.-tert-Butoxycarbonyl-L-(S-trityl)cysteinate and the Conformation-Stabilizing Function of Weak Intermolecular Bonding.

The Molecular and Crystal Structure of tert-Butyl N.ALPHA.-tert-Butoxycarbonyl-L-(S-trityl)cysteinate and the Conformation-Stabilizing Function of Weak Intermolecular Bonding.

Thermal behavior and polymorphism in medium–high temperature range of the sulfur containing amino acids l-cysteine and l-cystine

Multicomponent organic crystals at high pressure

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