Benzyl-L-proline
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Benzyl-L-proline

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Category
Cyclic Amino Acids
Catalog number
BAT-003425
CAS number
31795-93-4
Molecular Formula
C12H15NO2
Molecular Weight
205.30
Benzyl-L-proline
Synonyms
Bzl-L-Pro-OH; (S)-Benzyl-pyrrolidine-2-carboxylic acid
Appearance
White powder
Purity
≥ 99% (HPLC)
Density
1.205 g/cm3
Melting Point
168-171°C
Boiling Point
343.1±35.0 °C(Predicted)
Storage
Store at 2-8°C
Application
A reagent for the synthesis of optically pure α-amino-acids.
InChI
InChI=1S/C12H15NO2/c14-12(15)11-7-4-8-13(11)9-10-5-2-1-3-6-10/h1-3,5-6,11H,4,7-9H2,(H,14,15)/t11-/m0/s1
InChI Key
XNROFTAJEGCDCT-NSHDSACASA-N
Canonical SMILES
C1CC(N(C1)CC2=CC=CC=C2)C(=O)O
1. Supramolecular sheets in (4H-chromeno[4,3-c]isoxazol-3-yl)methanol and its hydrated 8-methyl-substituted analogue at 100 K
P Rajalakshmi, N Srinivasan, R V Krishnakumar, Ibrahim Abdul Razak, Mohd Mustaqim Rosli Acta Crystallogr C. 2012 Nov;68(Pt 11):o481-4. doi: 10.1107/S0108270112043545. Epub 2012 Oct 30.
The title compounds, (4H-chromeno[4,3-c]isoxazol-3-yl)methanol, C(11)H(9)NO(3), (I), and (8-methyl-4H-chromeno[4,3-c]isoxazol-3-yl)methanol monohydrate, C(12)H(11)NO(3)·H(2)O, (II), crystallize in the monoclinic space groups P2(1)/c and C2/c, respectively. The simple addition of a methyl substituent in (II) results in a change in the structure type and substantially alters the intermolecular interaction patterns, while retaining the point-group symmetry 2/m. Compound (II) crystallizes as a hydrate and the resulting hydrogen-bonding interactions involving the water molecule are the cause of differences in the hydrogen-bonded supramolecular motifs present in (I) and (II). The water molecule in (II) is disordered over two positions having very similar orientations, with occupancies of 0.571 (18) and 0.429 (18), although the pattern of hydrogen-bonding interactions for the two disordered water molecules remains essentially the same. In both compounds, the primary donor hydroxy group adopts a trans conformation with respect to the isoxazole O atom, with a torsion angle of 170.65 (8)° for (I) and 179.56 (10)° for (II), the small difference being due to differences in the hydrogen-bonding environment of the hydroxy group. In (I), molecules are linked through two independent O-H···N and C-H···O hydrogen bonds and form sheets of centrosymmetric R(4)(4)(18) and R(4)(4)(14) rings extending parallel to the (100) plane. The supramolecular motifs in (II) generate two-dimensional sheets parallel to the (100) plane through a combination of O-H···X (X = N, O) and C-H···O hydrogen bonds, leading to water-assisted noncentrosymmetric R(2)(2)(8) and R(6)(6)(20) motifs. The present work is an example of how the simple replacement of a substituent in the main molecular scaffold may transform the structure type, paving the way for a variety of supramolecular motifs and consequently altering the complexity of the intermolecular interaction patterns.
2. Crystal structure of N-(1-deoxy-beta-D-fructopyranos-1-yl)-L-proline-an Amadori compound
Mirosław Tarnawski, Katarzyna Slepokura, Tadeusz Lis, Renata Kuliś-Orzechowska, Bogdan Szelepin Carbohydr Res. 2007 Jul 2;342(9):1264-70. doi: 10.1016/j.carres.2007.03.007. Epub 2007 Mar 12.
Here we report the crystal structure data on N-(1-deoxy-beta-D-fructopyranos-1-yl)-L-proline (Fru-Pro)-an Amadori compound. X-ray crystal and molecular structures of its two isomorphous crystalline forms, (Fru-Pro)xMeOH, C(11)H(19)NO(7)xCH(4)O (1a) and (Fru-Pro)x2H(2)O, C(11)H(19)NO(7)x2H(2)O (1b) were determined. In 1a and 1b the compound crystallizes as the beta-anomer with the overall geometry of Fru-Pro zwitterions being very similar. Fructose ring adopts the chair (2)C(5) conformation with the proline moiety bonded to equatorial C-1 atom and remaining in a trans-gauche (tg) orientation with respect to the sugar ring. The five-membered pyrrolidine ring adopts an envelope conformation, with the Cbeta atom puckered. Fructosyl and carboxylate groups are in bisectional and axial positions of pyrrolidine ring, respectively. The overall molecular geometry of Fru-Pro zwitterions, especially the relative orientation of sugar and amino acid moieties, is stabilized by intramolecular, three-centred N-H...O(Fru)/O(Pro) hydrogen bonds (with bifurcated acceptor) formed between aminium and hydroxyl/carboxylate groups. The packing diagrams are very similar in both 1a and 1b with the adjacent zwitterions linked to each other by the extensive network of O-H...O and C-H...O hydrogen bonds to form channels along the a-axis, filled up with solvent molecules.
3. Chiral one- and two-dimensional silver(I)-biotin coordination polymers
Muhammad Altaf, Helen Stoeckli-Evans Acta Crystallogr C. 2013 Feb;69(Pt 2):127-37. doi: 10.1107/S0108270113000322. Epub 2013 Jan 22.
Reaction of biotin {C(10)H(16)N(2)O(3)S, HL; systematic name: 5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoic acid} with silver acetate and a few drops of aqueous ammonia leads to the deprotonation of the carboxylic acid group and the formation of a neutral chiral two-dimensional polymer network, poly[[{μ(3)-5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoato}silver(I)] trihydrate], {[Ag(C(10)H(15)N(2)O(3)S)]·3H(2)O}(n) or {[Ag(L)]·3H(2)O}(n), (I). Here, the Ag(I) cations are pentacoordinate, coordinated by four biotin anions via two S atoms and a ureido O atom, and by two carboxylate O atoms of the same molecule. The reaction of biotin with silver salts of potentially coordinating anions, viz. nitrate and perchlorate, leads to the formation of the chiral one-dimensional coordination polymers catena-poly[[bis[nitratosilver(I)]-bis{μ(3)-5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoato}] monohydrate], {[Ag(2)(NO(3))(2)(C(10)H(16)N(2)O(3)S)(2)]·H(2)O}(n) or {[Ag(2)(NO(3))(2)(HL)(2)]·H(2)O}(n), (II), and catena-poly[bis[perchloratosilver(I)]-bis{μ(3)-5-[(3aS,4S,6aR)-2-oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl]pentanoato}], [Ag(2)(ClO(4))(2)(C(10)H(16)N(2)O(3)S)(2)](n) or [Ag(2)(ClO(4))(2)(HL)(2)](n), (III), respectively.
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