The crystal structure of hexagonal<scp>L</scp>-cystine

Oughton, Beryl M.; Harrison, Pauline M.

doi:10.1107/s0365110x59001177

Cited by 99 publications

(61 citation statements)

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“…Tables of anisotropic temperature factors, hydrogen atom positional parameters, bond lengths and bond angles involving hydrogen, torsional angles and the moduli of F, and F, have been deposited and are available on request, at a nominal charge, from the ~e~o s i t o r y of Unpublished Data, CISTI, National Research Council of Canada, Ottawa, Ont., been determined (17). We have compared our structure with these structures and also with those of the two forms of cystine (18)(19)(20), the protonated chloride and bromide salts of cystine (21 -24), and N,N1-diglycyl-L-cystine (25). Most bond lengths and angles agree remarkably well with equivalent distances in the above compounds.…”

Section: Discussionmentioning

confidence: 48%

Structural and spectroscopic studies of dipotassium 3,3,3′,3′-tetramethylcystinate trihydrate, K₂[C₁₀H₁₈N₂O₄S₂]3H₂O

Faggiani¹,

Howard-Lock²,

Lock³

et al. 1984

Can. J. Chem.

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127 (1984). The compound dipotassium 3,3,3',3'-tetramethylcystinate trihydrate, K2 [CII,H,,0,N2S2]3H20, has been prepared and characterized by single crystal X-ray diffraction. Crystals were monoclinic, P 2 , , n = 6.160(1), b = 26.473(8), c = 6.193(1) A, P = 113.94(1)", with two formula units in the unit cell. Intensities were measured on a Syntex P2[ diffractometer with use of MoKa radiation. The structure was solved by standard methods and refined to RI = 0.0469, R2 = 0.0472 based on 2303 independent observed reflections. The C-S bonds (1.877(6), 1.891(6) A) are longer than in many similar compounds although the S-S bond (2.040(2) A) is not. The C-S-S-C torsional angle (108.7(3)") is larger than normal in dithiol compounds. Other distances and angles are normal. Two types of potassium coordination are present, one a distorted octahedron, the other a distorted trigonal prism. In addition to the ionic interactions, hydrogen bonds involving the water molecules are important in stabilizing the structure. (108,7(3)") est plus grand que ceux observts normalement dans les dithiols. Les autres distances et les autres angles sont normaux. Le potassium posskde deux types de coordination, I'un est un octakdre deform6 tandis que I'autre est un prisme trigonal dCformC. En plus des interactions ioniques, les liaisons hydrogknes impliquant les molCcules d'eau sont importantes pour de la stabilitC de la structure.[Traduit par le journal]

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Section: Discussionmentioning

confidence: 48%

Structural and spectroscopic studies of dipotassium 3,3,3′,3′-tetramethylcystinate trihydrate, K₂[C₁₀H₁₈N₂O₄S₂]3H₂O

Faggiani¹,

Howard-Lock²,

Lock³

et al. 1984

Can. J. Chem.

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“…This differs from conformations reported for similar structures. For example, in the cysteinyl residue ofglutathione (Wright, 1958), hexagonal L-cystine (Oughton & Harrison, 1959), L-cystine hydrobromide (Peterson, Steinrauf & Jensen, 1960) and in N,N'-diglycylcystine (Yakel & Hughes, 1954) the sulfur is always trans to the or-hydrogen. (a) Ueki et al (1969).…”

Section: Side-chain Conformationsmentioning

confidence: 99%

The crystal structure of S-benzyl-L-cysteinyl-L-prolyl-L-leucylglycinamide and its selenium analog

Rudko¹,

Low²

1975

Acta Crystallogr Sect B

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The crystal structure of the protected C-terminal tetrapeptide fragment of oxytocin, S-benzyl-L-cysteinyl-L-prolyl-L-leucylglycinamide, has been determined, as well as that of the analogous peptide in which sulfur is replaced by selenium. The crystals of both compounds are monoclinic, space group P21. Lattice constants are a= 13.65, b=8.97, c=20.27 A,, fl=93.33 ° for the sulfur peptide and a= 13.71, b = 9.07, c= 20.31A., fl= 94-00 ° for the nearly isomorphous selenium peptide. The selenium analog structure was solved by the heavy-atom method. The atomic parameters so derived were used as a starting point for the refinement of both structures. The least-squares refinement was not straightforward; the selenium peptide would refine to an R value of only 0.21, while the sulfur peptide was finally refined to an R value of 0.085. There are two molecules in the asymmetric unit with very similar conformations and orientations, related by a translation of approximately ¼b+½c. The peptides are in a compact '3L0 bend' conformation with an intramolecular hydrogen bond between the carbonyl oxygen of the cysteinyl residue and the amide nitrogen of the leucyl residue. In one of the molecules in the asymmetric unit there is a second hydrogen bond between the carbonyl oxygen of the prolyl residue and the C-terminal amide nitrogen.

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“…A value of about 103 ° has been observed in other cystine compounds: N,N'-diglycyl-L-cystine dihydrate (Yakel & Hughes, 1954), L-cystine dihydrochloride (Steinrauf, Peterson & Jensen, 1958), L-cystine dihydrobromide (Peterson, Steinrauf & Jensen, 1960), L-cystinediamide dihydrochloride (Chaney & Steinrauf, 1968) and tetragonal L-cystine (Chaney & Steinrauf, 1974). But the value (114 °) observed in the case of hexagonal L-cystine (Oughton & Harrison, 1959) differs from these.…”

Section: (B) Bond Distances and Anglesmentioning

confidence: 92%

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

Vijayalakshmi¹,

Srinivasan²

1975

Acta Crystallogr Sect B

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CaHI6N204S2.2HC1. H20 is monoclinic, space group P21, with a = 14"80, b = 9.34, c = 5.85/~, fl= 91.47 °, Z= 2. The structure was solved by the heavy-atom method and refined by block-diagonal least-squares calculations to a final R of 0.103 for 1620 observed reflexions. The structure is stabilized by an extensive network of hydrogen bonds. The disulphide dihedral angle is 84-4 °. The helical sense of the cystinyI group in the molecule is 'left'.

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The crystal structure of hexagonalL-cystine

Cited by 99 publications

References 1 publication

Structural and spectroscopic studies of dipotassium 3,3,3′,3′-tetramethylcystinate trihydrate, K₂[C₁₀H₁₈N₂O₄S₂]3H₂O

Structural and spectroscopic studies of dipotassium 3,3,3′,3′-tetramethylcystinate trihydrate, K₂[C₁₀H₁₈N₂O₄S₂]3H₂O

The crystal structure of S-benzyl-L-cysteinyl-L-prolyl-L-leucylglycinamide and its selenium analog

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

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The crystal structure of hexagonalL-cystine

Cited by 99 publications

References 1 publication

Structural and spectroscopic studies of dipotassium 3,3,3′,3′-tetramethylcystinate trihydrate, K2[C10H18N2O4S2]3H2O

Structural and spectroscopic studies of dipotassium 3,3,3′,3′-tetramethylcystinate trihydrate, K2[C10H18N2O4S2]3H2O

The crystal structure of S-benzyl-L-cysteinyl-L-prolyl-L-leucylglycinamide and its selenium analog

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

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Structural and spectroscopic studies of dipotassium 3,3,3′,3′-tetramethylcystinate trihydrate, K₂[C₁₀H₁₈N₂O₄S₂]3H₂O

Structural and spectroscopic studies of dipotassium 3,3,3′,3′-tetramethylcystinate trihydrate, K₂[C₁₀H₁₈N₂O₄S₂]3H₂O