Z-L-phenylalanine methyl ester
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Z-L-phenylalanine methyl ester

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Category
CBZ-Amino Acids
Catalog number
BAT-003369
CAS number
35909-92-3
Molecular Formula
C18H19NO4
Molecular Weight
313.35
Z-L-phenylalanine methyl ester
IUPAC Name
methyl (2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
Synonyms
Z-L-Phe-Ome; N-(Benzyloxycarbonyl)-L-Phenylalanine Methyl Ester; Methyl (2S)-3-Phenyl-2-(Phenylmethoxycarbonylamino)Propanoate
Appearance
Yellowish oil
Purity
≥ 97% (HPLC)
Density
1.182 g/cm3
Boiling Point
478.541°C
Storage
Store at 2-8 °C
InChI
InChI=1S/C18H19NO4/c1-22-17(20)16(12-14-8-4-2-5-9-14)19-18(21)23-13-15-10-6-3-7-11-15/h2-11,16H,12-13H2,1H3,(H,19,21)/t16-/m0/s1
InChI Key
BBACSHIJBOGXKL-INIZCTEOSA-N
Canonical SMILES
COC(=O)C(CC1=CC=CC=C1)NC(=O)OCC2=CC=CC=C2
1. Pseudopolymorphism of N-acetyl-L-phenylalanine methyl ester
Alicja Janik, Monika Jarocha, Katarzyna Stadnicka Acta Crystallogr B. 2008 Apr;64(Pt 2):223-9. doi: 10.1107/S010876810800219X. Epub 2008 Mar 14.
The structures of two pseudopolymorphs of N-acetyl-L-phenylalanine methyl ester, L-AcFOMe, were determined at both 293 (2) and 150 (2) K. At room temperature, the orthorhombic phase C(12)H(15)NO(3) (I), with space group P2(1)2(1)2(1), converts into the tetragonal phase C(12)H(15)NO(3).0.5H(2)O (II), with space group P4(1)2(1)2, in the presence of water. In the structures of both pseudopolymorphs, alternating layers of hydrophilic and hydrophobic intermolecular interaction can be distinguished. In the hydrophilic layers the structures are stabilized by moderate hydrogen bonds of the type N-H...O for the anhydrous L-AcFOMe and of types N-H...O and O-H...O for the hemihydrate. Weak C-H...pi interactions are observed within the hydrophobic layers: for (I) they are of type III [Malone et al. (1997). J. Chem. Soc. Faraday Trans. 93, 3429-3436], whereas typical type I edge-to-face interactions are present for (II). The differences between the hydrogen-bonding networks of (I) and (II) are discussed in terms of graph-set analysis.
2. Standard Thermodynamic Functions of Tripeptides N-Formyl-l-methionyl-l-leucyl-l-phenylalaninol and N-Formyl-l-methionyl-l-leucyl-l-phenylalanine Methyl Ester
Alexey V Markin, Evgeny Markhasin, Semen S Sologubov, Natalia N Smirnova, Robert G Griffin J Chem Eng Data. 2014 Apr 10;59(4):1240-1246. doi: 10.1021/je400879v. Epub 2014 Mar 13.
The heat capacities of tripeptides N-formyl-l-methionyl-l-leucyl-l-phenylalaninol (N-f-MLF-OH) and N-formyl-l-methionyl-l-leucyl-l-phenylalanine methyl ester (N-f-MLF-OMe) were measured by precision adiabatic vacuum calorimetry over the temperature range from T = (6 to 350) K. The tripeptides were stable over this temperature range, and no phase change, transformation, association, or thermal decomposition was observed. The standard thermodynamic functions: molar heat capacity Cp,m, enthalpy H(T) - H(0), entropy S(T), and Gibbs energy G(T) - H(0) of peptides were calculated over the range from T = (0 to 350) K. The low-temperature (T ≤ 50 K) heat capacities dependencies were analyzed using the Debye's and the multifractal theories. The standard entropies of formation of peptides at T = 298.15 K were calculated.
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