Z-L-Tyrosine tert-butyl ester hydrate
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Z-L-Tyrosine tert-butyl ester hydrate

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Category
CBZ-Amino Acids
Catalog number
BAT-003388
CAS number
350819-37-3
Molecular Formula
C21H25NO5·H2O
Molecular Weight
389.44
Z-L-Tyrosine tert-butyl ester hydrate
IUPAC Name
tert-butyl (2S)-3-(4-hydroxyphenyl)-2-(phenylmethoxycarbonylamino)propanoate;hydrate
Alternative CAS
16881-33-7
Synonyms
Z-L-Tyr-OtBu H2O; (S)-Tert-Butyl 2-(Benzyloxycarbonylamino)-3-(4-Hydroxyphenyl)Propanoate Hydrate
Appearance
White powder
Purity
≥ 99% (HPLC)
Melting Point
75-89 ºC
Storage
Store at 2-8 °C
InChI
InChI=1S/C21H25NO5.H2O/c1-21(2,3)27-19(24)18(13-15-9-11-17(23)12-10-15)22-20(25)26-14-16-7-5-4-6-8-16;/h4-12,18,23H,13-14H2,1-3H3,(H,22,25);1H2/t18-;/m0./s1
InChI Key
KLOCNHOHUOPWHZ-FERBBOLQSA-N
Canonical SMILES
CC(C)(C)OC(=O)C(CC1=CC=C(C=C1)O)NC(=O)OCC2=CC=CC=C2.O
1. The achiral tetrapeptide Z-Aib-Aib-Aib-Gly-OtBu
Renate Gessmann, Hans Brückner, Kyriacos Petratos Acta Crystallogr C Struct Chem. 2014 Nov;70(Pt 11):1046-9. doi: 10.1107/S2053229614022165. Epub 2014 Oct 15.
The title achiral peptide N-benzyloxycarbonyl-α-aminoisobutyryl-α-aminoisobutyryl-α-aminoisobutyrylglycine tert-butyl ester or Z-Aib-Aib-Aib-Gly-OtBu (Aib is α-aminoisobutyric acid, Z is benzyloxycarbonyl, Gly is glycine and OtBu indicates the tert-butyl ester), C26H40N4O7, is partly hydrated (0.075H2O) and has two different conformations which together constitute the asymmetric unit. Both molecules form incipient 310-helices. They differ in the relative orientation of the N-terminal protection group and at the C-terminus. There are two 4→1 intramolecular hydrogen bonds.
2. Screening of solvents for favoring hydrolytic activity of Candida antarctica Lipase B
Bartłomiej Zieniuk, Agata Fabiszewska, Ewa Białecka-Florjańczyk Bioprocess Biosyst Eng. 2020 Apr;43(4):605-613. doi: 10.1007/s00449-019-02252-0. Epub 2019 Nov 16.
Lipases are a group of enzymes of considerable significance in organic synthesis, among which Candida antarctica lipase B (CALB) is one of the most widely studied enzymes. The activity of the biocatalyst has been intensively characterized in many organic media, but this paper aimed to compare the effect of 20 different solvents on the activity of CALB in the hydrolysis of p-nitrophenyl laurate. Nonpolar, polar aprotic, and polar protic solvents were used for enzyme pretreatment and then entered the composition of mixed solvents reaction medium. An impact of solvents on solvation processes affecting the catalysis steps, protein denaturation, and changes of its conformation was discussed. Moreover the hydrolytic activity of CALB with partition coefficient (logP) of the solvent used was correlated. It was emphasized that the substrate solubility plays an important role in solvent selection. In the presence of hydrophobic solvents, hydration layer becomes more hydrophobic facilitating the substrate access to the enzyme surface. In turn, polar compounds are good solvents for organic substrates facilitating the penetration of the aqueous layer that surrounds the surface of the enzyme. Two variants proved to be favorable for ester hydrolysis reaction: isooctane or polar solvent such as acetone, tert -butyl methyl ether, tert-butanol or acetonitrile.
3. Acetonitrile hydration and ethyl acetate hydrolysis by pyrazolate-bridged cobalt(II) dimers containing hydrogen-bond donors
Paul J Zinn, Thomas N Sorrell, Douglas R Powell, Victor W Day, A S Borovik Inorg Chem. 2007 Nov 26;46(24):10120-32. doi: 10.1021/ic700685g. Epub 2007 Nov 1.
The preparation of new CoII-mu-OH-CoII dimers with the binucleating ligands 3,5-bis{bis[(N'-R-ureaylato)-N-ethyl]aminomethyl}-1H-pyrazolate ([H4PRbuam]5-, R=tBu, iPr) is described. The molecular structure of the isopropyl derivative reveals that each CoII center has a trigonal-bipyramidial coordination geometry, with a Co...Co separation of 3.5857(5) A. Structural and spectroscopic studies show that there are four hydrogen-bond (H-bond) donors near the CoII-micro-OH-CoII moiety; however, they are too far away to be form intramolecular H-bonds with the bridging hydroxo ligand. Treating [CoII2H4PRbuam(micro-OH)]2- with acetonitrile led to the formation of bridging acetamidato complexes, [CoII2H4PRbuam(micro-1,3-OC(NH)CH3)]2-; in addition, these CoII-micro-OH-CoII dimers hydrolyze ethyl acetate to form CoII complexes with bridging acetato ligands. The CoII-1,3-micro-X'-CoII complexes (X'=OAc-, [OC(NH)CH3]-) were prepared independently by reacting [CoII2H3PRbuam]2- with acetamide or [CoII2H4PRbuam]- with acetate. X-ray diffraction studies show that the orientation of the acetate ligand within the H-bonding cavity depends on the size of the R substituent appended from the urea groups. The tetradentate ligand 3-{bis[(N'-tert-butylureaylato)-N-ethyl]aminomethyl}-5-tert-butyl-1H-pyrazolato ([H2PtBuuam]3-) was also developed and its CoII-OH complex prepared. In the crystalline state, [CoIIH2PtBuuam(OH)]2- contains two intramolecular H-bonds between the urea groups of [H2PtBuuam]3- and the terminal hydroxo ligand. [nPr4N]2[CoIIH2PtBuuam(OH)] does not hydrate acetonitrile or hydrolyze ethyl acetate. In contrast, K2[CoIIH2PtBuuam(OH)] does react with ethyl acetate to produce KOAc; this enhanced reactivity is attributed to the presence of the K+ ions, which can possibly interact with the CoII-OH unit and ester substrate to assist in hydrolysis. However, K2[CoIIH2PtBuuam(OH)] was still unable to hydrate acetonitrile.
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