L-Alanine benzyl ester hydrochloride
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L-Alanine benzyl ester hydrochloride

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A benzoxazine derivative used as an additive in the microemulsion formulation for topical applications of acyclovir. A reagent in the preparation of collagenase inhibitors.

Category
L-Amino Acids
Catalog number
BAT-003951
CAS number
5557-83-5
Molecular Formula
C10H13NO2·HCl
Molecular Weight
215.90
L-Alanine benzyl ester hydrochloride
IUPAC Name
benzyl (2S)-2-aminopropanoate;hydrochloride
Synonyms
L-Ala-OBzl HCl; L-Alanine benzyl ester hydrochloride
Appearance
White to off-white powder
Purity
≥ 98% (HPLC)
Density
1.1 g/cm3
Melting Point
136-145 °C
Boiling Point
293.0 °C at 760 mmHg
Storage
Store at 2-8 °C
InChI
InChI=1S/C10H13NO2.ClH/c1-8(11)10(12)13-7-9-5-3-2-4-6-9;/h2-6,8H,7,11H2,1H3;1H/t8-;/m0./s1
InChI Key
RLMHWGDKMJIEHH-QRPNPIFTSA-N
Canonical SMILES
CC(C(=O)OCC1=CC=CC=C1)N.Cl

L-Alanine benzyl ester hydrochloride, a versatile chemical compound with applications spanning bioscience and related fields. Explore its diverse utility through high perplexity and burstiness:

Peptide Synthesis: A cornerstone in peptide and protein synthesis, L-Alanine benzyl ester hydrochloride plays a pivotal role as a building block. Its ester functionality streamlines coupling reactions during peptide bond formation, aiding researchers in crafting synthetic peptides for in-depth structural and functional investigations in the realms of biochemistry and pharmacology.

Chemical Research: A key reagent in organic synthesis, particularly in the domain of asymmetric synthesis, this compound contributes to the creation of chiral intermediates crucial for producing enantiomerically pure compounds. Such research endeavors are instrumental in the development of novel drugs and materials with distinct chiral properties, pushing the boundaries of chemical exploration.

Pharmaceutical Development: Within drug design and development, L-Alanine benzyl ester hydrochloride emerges as a valuable precursor and intermediate, offering structural advantages for synthesizing prodrugs. These biologically inactive compounds can be metabolized into active drugs within the body, enhancing drug delivery efficacy and revolutionizing pharmaceutical treatment methodologies.

Biochemical Studies: Enzymology finds a vital tool in L-Alanine benzyl ester hydrochloride for probing enzyme kinetics and mechanisms. By utilizing this compound as a substrate, researchers can characterize enzymes acting on alanine derivatives, unraveling crucial insights into enzyme specificity and catalytic mechanisms. This knowledge underpins the comprehension of metabolic pathways and the design of potent enzyme inhibitors, shaping the landscape of biochemical research.

1. Synthesis of ( R)-Boc-2-methylproline via a Memory of Chirality Cyclization. Application to the Synthesis of Veliparib, a Poly(ADP-ribose) Polymerase Inhibitor
Lawrence Kolaczkowski, Jufang Barkalow, David M Barnes, Anthony Haight, Wayne Pritts, Adam Schellinger J Org Chem. 2019 Apr 19;84(8):4837-4845. doi: 10.1021/acs.joc.8b02866. Epub 2019 Feb 19.
( R)-Boc-2-methylproline (3a) was synthesized in good yield with excellent stereochemical control from alanine benzyl ester hydrochloride 11. The process, which is based on a modification of one described by Kawabata, proceeds in four steps and requires no chromatography. The product ( R)-Boc-2-methylproline (3a) was then carried forward in three steps to produce veliparib 1, a poly(ADP-ribose) polymerase inhibitor.
2. Synthesis of polyamide supports for use in peptide synthesis and as peptide-resin conjugates for antibody production
P Kanda, R C Kennedy, J T Sparrow Int J Pept Protein Res. 1991 Oct;38(4):385-91. doi: 10.1111/j.1399-3011.1991.tb01518.x.
We have synthesized beaded, hydrophilic cross-linked, aminoalkyl polydimethylacrylamide supports upon which peptides have been assembled using standard Boc or Fmoc chemistry in automated equipment. The resins were prepared by the free radical-initiated co-polymerization of N,N-dimethylacrylamide, N,N'-bisacrylyl-1,3-diaminopropane, and a functional monomer which were contained in a reverse-phase, detergent-emulsified suspension. The functional monomers used were N-(2-(methylsulfonyl)ethyloxycarbonyl)-allyl-amine (MSC-allylamine), N-acrylyl-1,6-diaminohexane hydrochloride or N-methacrylyl-1,3-diamino-propane hydrochloride. The MSC protecting group was removed by treatment of the resin with methanolic base during workup. After coupling of N-alpha-t-butyloxycarbonyl-alanine (Boc-alanine), amino acid analyses gave resin loading capacities between 0.15 mmol/g and 1.4 mmol/g, depending on the concentration and composition of the functional monomer. The resulting polymers were highly swollen by polar solvents including aqueous buffers. Peptides were synthesized on these supports after attaching the first amino acid directly or through a cleavable ester linker. When the carboxyl-terminal amino acid was coupled as the 4-oxymethylbenzoic acid derivative, the peptide could be deprotected and remain attached to the hydrophilic polymer since the peptide-benzyl ester bond was stable to HF deprotection at 0 degrees in the presence of 10% anisole and 1% ethanedithiol. The resulting peptidyl-resin could be swollen in aqueous buffers and injected into animals for the production of antibodies.
3. An efficient enantioselective synthesis of ( S)-α-methyl-serine methyl ester hydrochloride via asymmetrically catalyzed amination
Qiong Xiao, Yi-Fan Tang, Ping Xie J Asian Nat Prod Res. 2020 Jan;22(1):61-68. doi: 10.1080/10286020.2019.1634058. Epub 2019 Jul 16.
We present the synthesis of enantiomerically pure (S)-α-methyl-serine methyl ester hydrochloride from 2-methyl-3-((4-(trifluoromethyl)benzyl)oxy)propanal and di-p-chlorobenzyl azodicarboxylate via asymmetrically catalyzed amination with naphthylalanine derivative catalyst. The application of the organocatalyst of D-3-(1-Naphthyl)-alanine is the key step in the synthesis and ensures the product is obtained with high levels of stereocontrol.
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