l-Tyrosine isopropyl ester

Nuñez-Dallos, N.; Wurst, K.; Quevedo, R.

doi:10.1107/S1600536812042377

Volume 68
Part 11
Page o3173
November 2012

Received 4 October 2012
Accepted 10 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 233 K
Mean (C-C) = 0.003 Å
R = 0.036
wR = 0.099
Data-to-parameter ratio = 8.3
Details

L-Tyrosine isopropyl ester

Nelson Nuñez-Dallos,^a Klaus Wurst ^b and Rodolfo Quevedo ^a ^*

^aUniversidad Nacional de Colombia, Sede Bogotá, Facultad de Ciencias, Departamento de Química, Cra 30 No. 45-03, Bogotá, 4-72 Colombia, and ^bInstitute of General, Inorganic and Theoretical Chemistry, University of Innsbruck, Innrain 80-82, 6020 Innsbruck, Austria
Correspondence e-mail: arquevedop@unal.edu.co

The title compound, C₁₂H₁₇NO₃, adopts a folded conformation with a C-C(NH₂)-C(=O)-O torsion angle of -95.9 (2)°. In the crystal, molecules are linked by an O-HN hydrogen bond, forming helical chains along the b-axis direction. Weak N-HO and C-HO hydrogen bonds are observed between the chains.

Related literature

For information about tyrosine alkyl esters as prodrugs and the structure and intermolecular interactions of L-tyrosine methyl ester compared to L-tyrosine and its ethyl and n-butyl esters, see: Nicolaï et al. (2011). For the n-butyl analogue, see: Qian et al. (2006). For macrocyclization of tyrosine alkyl esters with formaldehyde, see: Quevedo & Moreno-Murillo (2009); Nuñez-Dallos et al. (2012). For a related structure of tyramine, see: Quevedo et al. (2012).

Experimental

Crystal data

C₁₂H₁₇NO₃
M_r = 223.27
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.4539 (1) Å
b = 14.0521 (3) Å
c = 16.5163 (4) Å
V = 1265.79 (5) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 233 K
0.4 × 0.3 × 0.2 mm

Data collection

Nonius KappaCCD diffractometer
8375 measured reflections
1318 independent reflections
1271 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.099
S = 1.07
1318 reflections
158 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.17 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3ON1ⁱ	0.97 (4)	1.78 (4)	2.736 (3)	167 (3)
N1-H1NO3ⁱⁱ	0.88 (2)	2.27 (2)	3.106 (2)	157 (2)
N1-H2NO3ⁱⁱⁱ	0.89 (3)	2.46 (3)	3.336 (3)	171 (2)
C2-H2O1^iv	0.99	2.37	3.314 (3)	159
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x+1, y, z.

Data collection: COLLECT (Nonius, 1998); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO (Otwinowski & Minor, 1997) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5203 ).

Acknowledgements

We thank the Universidad Nacional de Colombia for the financial support (DIB research project No. 14178).

References

Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Nicolaï, B., Mahé, N., Céolin, R., Rietveld, I., Barrio, M. & Tamarit, J.-L. (2011). Struct. Chem. 22, 649-659.
Nonius (1998). COLLECT. Nonius BV Delft, The Netherlands.
Nuñez-Dallos, N., Reyes, A. & Quevedo, R. (2012). Tetrahedron Lett. 53, 530-533.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp 307-326. New York: Academic Press.
Qian, S.-S., Zhu, H.-L. & Tiekink, E. R. T. (2006). Acta Cryst. E62, o882-o884.
Quevedo, R. & Moreno-Murillo, B. (2009). Tetrahedron Lett. 50, 936-938.
Quevedo, R., Nuñez-Dallos, N., Wurst, K. & Duarte-Ruiz, A. (2012). J. Mol. Struct. 1029, 175-179.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds