Boc-L-prolinol
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Boc-L-prolinol

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A building block for the synthesis of novel nicotinic acetylcholine receptor ligands with cognition-enhancing properties.

Category
Amino Alcohol
Catalog number
BAT-000363
CAS number
69610-40-8
Molecular Formula
C10H19NO3
Molecular Weight
201.25
Boc-L-prolinol
IUPAC Name
tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
Synonyms
Boc-Pro-ol; N-Boc-L-prolinol; (S)-tert-butyl 2-(hydroxymethyl)pyrrolidine-1-carboxylate; (S)-1-Boc-2-pyrrolidinemethanol; tert-butyl (2S)-2-(hydroxymethyl)pyrrolidine-1-carboxylate
Appearance
White crystals
Purity
≥ 98 % (GC)
Density
1.084 g/cm3
Melting Point
58-66 ℃
Boiling Point
289.5 ℃ at 760 mmHg
Storage
Store at 2-8 ℃
InChI
InChI=1S/C10H19NO3/c1-10(2,3)14-9(13)11-6-4-5-8(11)7-12/h8,12H,4-7H2,1-3H3/t8-/m0/s1
InChI Key
BFFLLBPMZCIGRM-QMMMGPOBSA-N
Canonical SMILES
CC(C)(C)OC(=O)N1CCCC1CO
1. Enzymatic preparation of 5-hydroxy-L-proline, N-Cbz-5-hydroxy-L-proline, and N-Boc-5-hydroxy-L-proline from (α-N-protected)-L-ornithine using a transaminase or an amine oxidase
R L Hanson, R M Johnston, S L Goldberg, W L Parker, R N Patel Enzyme Microb Technol. 2011 May 6;48(6-7):445-53. doi: 10.1016/j.enzmictec.2011.03.007. Epub 2011 Mar 26.
N-Cbz-4,5-dehydro-L-prolineamide or N-Boc-4,5-dehydro-L-prolineamide are alternative key intermediates for the synthesis of saxagliptin, a dipeptidyl peptidase IV (DPP4) inhibitor recently approved for treatment of type 2 diabetes mellitus. An efficient biocatalytic method was developed for conversion of L-ornithine, N-α-benzyloxycarbonyl (Cbz)-L-ornthine, and N-α-tert-butoxycarbonyl (Boc)-L-ornithine to 5-hydroxy-L-proline, N-Cbz-5-hydroxy-L-proline, and N-Boc-5-hydroxy-L-proline, respectively. Rec. Escherichia coli expressing lysine-ε-aminotransferase and rec Pichia pastoris expressing L-ornithine oxidase were used for these conversions. N-Cbz-5-hydroxy-L-proline, and N-Boc-5-hydroxy-L-proline were chemically converted to key intermediates N-Cbz-4,5-dehydro-L-prolineamide and N-Boc-4,5-dehydro-L-prolineamide, respectively.
2. Microbial Proline Racemase-Proline Dehydrogenase Cascade for Efficient Production of D-proline and N-boc-5-hydroxy-L-proline from L-proline
Fanfan Zhang, Shiwen Xia, Hui Lin, Jiao Liu, Wenxin Huang Appl Biochem Biotechnol. 2022 Sep;194(9):4135-4146. doi: 10.1007/s12010-022-03980-y. Epub 2022 May 30.
D-proline and N-boc-5-hydroxy-L-proline are key chiral intermediates in the production of eletriptan and saxagliptin, respectively. An efficient proline racemase-proline dehydrogenase cascade was developed for the enantioselective production of D-proline. It included the racemization of L-proline to DL-proline and the enantioselective dehydrogenation of L-proline in DL-proline. The racemization of L-proline to DL-proline used an engineered proline racemase (ProR). L-proline up to 1000 g/L could be racemized to DL-proline with 1 g/L of wet Escherichia coli cells expressing ProR within 48 h. The efficient dehydrogenation of L-proline in DL-proline was achieved using whole cells of proline dehydrogenase-producing Pseudomonas pseudoalcaligenes XW-40. Moreover, using a cell-recycling strategy, D-proline was obtained in 45.7% yield with an enantiomeric excess of 99.6%. N-boc-5-hydroxy-L-proline was also synthesized from L-glutamate semialdehyde, a dehydrogenated product of L-proline, in a 16.7% yield. The developed proline racemase-proline dehydrogenase cascade exhibits great potential and economic competitiveness for manufacturing D-proline and N-boc-5-hydroxy-L-proline from L-proline.
3. Well-defined homopolypeptides, copolypeptides, and hybrids of poly(l-proline)
Manos Gkikas, Hermis Iatrou, Nikolaos S Thomaidis, Paschalis Alexandridis, Nikos Hadjichristidis Biomacromolecules. 2011 Jun 13;12(6):2396-406. doi: 10.1021/bm200495n. Epub 2011 May 25.
l-Proline is the only, out of 20 essential, amino acid that contains a cyclized substituted α-amino group (is formally an imino acid), which restricts its conformational shape. The synthesis of well-defined homo- and copolymers of l-proline has been plagued either by the low purity of the monomer or the inability of most initiating species to polymerize the corresponding N-carboxy anhydride (NCA) because they require a hydrogen on the 3-N position of the five-member ring of the NCA, which is missing. Herein, highly pure l-proline NCA was synthesized by using the Boc-protected, rather than the free amino acid. The protection of the amine group as well as the efficient purification method utilized resulted in the synthesis of highly pure l-proline NCA. The high purity of the monomer and the use of an amino initiator, which does not require the presence of the 3-N hydrogen, led for the first time to well-defined poly(l-proline) (PLP) homopolymers, poly(ethylene oxide)-b-poly(l-proline), and poly(l-proline)-b-poly(ethylene oxide)-b-poly(l-proline) hybrids, along with poly(γ-benzyl-l-glutamate)-b-poly(l-proline) and poly(Boc-l-lysine)-b-poly(l-proline) copolypeptides. The combined characterization (NMR, FTIR, and MS) that results for the l-proline NCA revealed its high purity. In addition, all synthesized polymers exhibit high molecular and compositional homogeneity.
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