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Crystal structure of methyl (S)-2-{(R)-4-[(tert-but-oxy-carbon-yl)amino]-3-oxo-1,2-thia-zolidin-2-yl}-3-methyl-butano-ate: a chemical model for oxidized protein tyrosine phosphatase 1B (PTP1B).

Ruddraraju KV, Hillebrand R, Barnes CL, Gates KS - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: Within the individual columns, there are also C-H⋯S and C-H⋯O hydrogen bonds present.The columns of A and B mol-ecules are linked by C-H⋯O hydrogen bonds, forming sheets parallel to (10-1).The absolute structure was determined by resonant scattering [Flack parameter = 0.00 (3)].

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Affiliation: 125 Chemistry Bldg, University of Missouri Columbia, MO 65211, USA.

ABSTRACT
The asymmetric unit of the title compound, C14H24N2O5S, contains two independent mol-ecules (A and B). In each mol-ecule, the iso-thia-zolidin-3-one ring adopts an envelope conformation with the methyl-ene C atom as the flap. In the crystal, the A mol-ecules are linked to one another by N-H⋯O hydrogen bonds, forming columns along [010]. The B mol-ecules are also linked to one another by N-H⋯O hydrogen bonds, forming columns along the same direction, i.e. [010]. Within the individual columns, there are also C-H⋯S and C-H⋯O hydrogen bonds present. The columns of A and B mol-ecules are linked by C-H⋯O hydrogen bonds, forming sheets parallel to (10-1). The absolute structure was determined by resonant scattering [Flack parameter = 0.00 (3)].

No MeSH data available.


A view of the mol­ecular structure of the two independent mol­ecules (A and B) of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
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fig1: A view of the mol­ecular structure of the two independent mol­ecules (A and B) of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Mentions: The mol­ecular structures of the two independent mol­ecules (A and B) of the title compound are shown in Fig. 1 ▸. The two mol­ecules differ only in the orientation of the isopropyl group (Fig. 1 ▸). The bond lengths and angles are very similar to those seen in the crystal structures of the oxidized enzyme PTP1B (see: pdb codes 1oem, 1oes, 3sme). In both mol­ecules, the iso­thio­zolidin-3-one ring adopts an envelope conformation with the methyl­ene C atom (C1A in mol­ecule A and C1B in mol­ecule B) as the flap, similar to the conformation of oxidized PTP1B (pdb code: 1oem). In previously reported chemical models (1,2-benziso­thia­zole compounds) of PTP1B, the five-membered ring is planar (Kim et al., 1996 ▸; Ranganathan et al., 2002 ▸; Wang et al., 2011 ▸; Sivaramakrishnan et al., 2005 ▸). The S—N bond lengths in the title compound [S1A—N1A = 1.740 (2) Å and S1B—N1B = 1.733 (2) Å], are similar to the same bond distance of ca 1.71 Å in oxidized PTP1B (pdb code: 1oem).


Crystal structure of methyl (S)-2-{(R)-4-[(tert-but-oxy-carbon-yl)amino]-3-oxo-1,2-thia-zolidin-2-yl}-3-methyl-butano-ate: a chemical model for oxidized protein tyrosine phosphatase 1B (PTP1B).

Ruddraraju KV, Hillebrand R, Barnes CL, Gates KS - Acta Crystallogr E Crystallogr Commun (2015)

A view of the mol­ecular structure of the two independent mol­ecules (A and B) of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4518936&req=5

fig1: A view of the mol­ecular structure of the two independent mol­ecules (A and B) of the title compound. Displacement ellipsoids are drawn at the 50% probability level.
Mentions: The mol­ecular structures of the two independent mol­ecules (A and B) of the title compound are shown in Fig. 1 ▸. The two mol­ecules differ only in the orientation of the isopropyl group (Fig. 1 ▸). The bond lengths and angles are very similar to those seen in the crystal structures of the oxidized enzyme PTP1B (see: pdb codes 1oem, 1oes, 3sme). In both mol­ecules, the iso­thio­zolidin-3-one ring adopts an envelope conformation with the methyl­ene C atom (C1A in mol­ecule A and C1B in mol­ecule B) as the flap, similar to the conformation of oxidized PTP1B (pdb code: 1oem). In previously reported chemical models (1,2-benziso­thia­zole compounds) of PTP1B, the five-membered ring is planar (Kim et al., 1996 ▸; Ranganathan et al., 2002 ▸; Wang et al., 2011 ▸; Sivaramakrishnan et al., 2005 ▸). The S—N bond lengths in the title compound [S1A—N1A = 1.740 (2) Å and S1B—N1B = 1.733 (2) Å], are similar to the same bond distance of ca 1.71 Å in oxidized PTP1B (pdb code: 1oem).

Bottom Line: Within the individual columns, there are also C-H⋯S and C-H⋯O hydrogen bonds present.The columns of A and B mol-ecules are linked by C-H⋯O hydrogen bonds, forming sheets parallel to (10-1).The absolute structure was determined by resonant scattering [Flack parameter = 0.00 (3)].

View Article: PubMed Central - HTML - PubMed

Affiliation: 125 Chemistry Bldg, University of Missouri Columbia, MO 65211, USA.

ABSTRACT
The asymmetric unit of the title compound, C14H24N2O5S, contains two independent mol-ecules (A and B). In each mol-ecule, the iso-thia-zolidin-3-one ring adopts an envelope conformation with the methyl-ene C atom as the flap. In the crystal, the A mol-ecules are linked to one another by N-H⋯O hydrogen bonds, forming columns along [010]. The B mol-ecules are also linked to one another by N-H⋯O hydrogen bonds, forming columns along the same direction, i.e. [010]. Within the individual columns, there are also C-H⋯S and C-H⋯O hydrogen bonds present. The columns of A and B mol-ecules are linked by C-H⋯O hydrogen bonds, forming sheets parallel to (10-1). The absolute structure was determined by resonant scattering [Flack parameter = 0.00 (3)].

No MeSH data available.