Boc-alpha-Me-L-Pro-OH

Boc-alpha-Me-L-Pro-OH is a protected amino acid derivative of L-proline bearing an N-Boc (tert-butoxycarbonyl) protecting group and an alpha-methyl substitution, classifying it as a Boc-protected, non-unmodified proline analogue used as a peptide-building block. The molecule contains a free carboxylic acid and a Boc-protected amino functionality, while the pyrrolidine ring provides a cyclic secondary amine side-chain framework and the alpha-methyl group constrains the backbone conformation. In peptide synthesis workflows, the Boc group supports chemoselective, stepwise coupling by masking the amino group during assembly, and the alpha-methyl substitution is used in structure-activity and conformational studies to modulate peptide backbone geometry.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

CAT No: CP25124

CAS No:103336-06-7

Synonyms/Alias:103336-06-7;(S)-1-(tert-butoxycarbonyl)-2-methylpyrrolidine-2-carboxylicacid;N-BOC-ALPHA-METHYL-L-PROLINE;1-Boc-2-methyl-L-proline;1-(TERT-BUTOXYCARBONYL)-2-METHYL-L-PROLINE;N-BOC-2-METHYL-L-PROLINE;Ambcb4042454;N-Boc-|A-methyl-L-proline;SCHEMBL387543;BOC-ALPHA-ME-L-PRO-OH;N-BOC-A-METHYL-L-PROLINE;MolPort-016-631-569;YQXRKJHVAUKXRN-NSHDSACASA-N;ZINC391234;(S)-N-BOC-2-METHYLPROLINE;N-tert-butoxycarbonyl-2-methylproline;AKOS015999983;CB-2574;PB32674;QC-4614;1-(tert-butoxycarbonyl)-2-methylproline;AJ-21073;AK-90256;HE075146;AB0083258

Chemical Name:N-alpha-t-Butyloxycarbonyl-alpha-Methyl-L-proline

Custom Peptide Synthesis
cGMP Peptide
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M.F/Formula
C11H19NO4
M.W/Mr.
229,27 g/mole

Boc-alpha-Me-L-Pro-OH is a Boc-protected, stereochemically defined amino acid derivative built on the L-proline scaffold with an alpha-methyl substitution. The Boc group provides an N-terminal protecting strategy that is routinely used to control reactivity during peptide assembly, while the constrained proline ring and alpha-methyl motif help introduce steric and conformational effects in downstream sequences. This reagent is therefore used primarily as a protected amino acid building block for constructing modified peptides and for preparing well-defined pharmaceutical and research intermediates.

1. Solid-Phase Peptide Synthesis

Boc-alpha-Me-L-Pro-OH is frequently selected by peptide synthesis groups for solid-phase peptide synthesis workflows where controlled N-terminus protection is required for coupling into growing chains. The Boc-protected amino terminus allows the residue to be handled as a stable building block during stepwise assembly, enabling incorporation of an alpha-methyl proline unit that can influence local backbone geometry and peptide conformational preferences. Custom peptide manufacturers and academic peptide chemistry labs use this type of residue to generate sequence-defined analogs for structure-activity relationship studies and for producing modified peptide standards for downstream characterization.

2. Modified Peptide Library Construction

Boc-alpha-Me-L-Pro-OH supports medicinal chemistry and chemical biology efforts that build peptide libraries containing sterically tuned proline analogs. By introducing an alpha-methyl substituent on the proline backbone, this building block helps researchers access analog series where subtle changes in sterics and conformational bias are evaluated across a common scaffold. Peptide discovery teams commonly rely on protected amino acid derivatives like this to streamline parallel synthesis of analogs, ensuring consistent residue identity and minimizing variability between library members during purification and analytical verification.

3. Pharmaceutical Intermediate Development

Boc-alpha-Me-L-Pro-OH is used in pharmaceutical intermediate development as a protected amino acid building block for preparing defined peptide fragments and advanced coupling partners used in larger synthetic routes. Process development and custom synthesis organizations favor Boc-protected amino acid derivatives because the protecting group provides practical control over chemoselectivity during fragment construction and subsequent transformations. This product is particularly relevant when an alpha-methyl proline motif is required in a late-stage intermediate, enabling reproducible assembly of modified peptide components for research-grade lead optimization materials.

Size
1 g;5 g;
InChI
1S/C11H19NO4/c1-10(2,3)16-9(15)12-7-5-6-11(12,4)8(13)14/h5-7H2,1-4H3,(H,13,14)/t11-/m0/s1
InChI Key
YQXRKJHVAUKXRN-NSHDSACASA-N
Canonical SMILES
CC1(CCCN1C(=O)OC(C)(C)C)C(=O)O

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