Boc-D-Met-Gly-OH

Boc-D-Met-Gly-OH is a protected dipeptide-like amino acid derivative consisting of a D-methionine residue linked to glycine, where the N-terminus is capped with a Boc (tert-butoxycarbonyl) protecting group. The molecule contains a free carboxylic acid at the terminal glycine position and an amide linkage between the two amino acid units, with methionine's thioether side chain providing a sulfur-containing functionality that can participate in chemical transformations typical of thioethers. Boc-D-Met-Gly-OH is used as a stepwise building block in peptide synthesis workflows and as a defined intermediate for preparing larger peptide derivatives and for analytical or structure-activity studies requiring a specific protected methionine-glycine motif with defined N-terminal protection.

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

CAT No: CP27368

CAS No:69612-71-1

Synonyms/Alias:Boc-D-Met-Gly-OH;69612-71-1;BOC-D-METHIONYL-GLYCINE;SCHEMBL10606688;C12H22N2O5S;CTK7B5630;ZINC2556551;6342AH;KM1292

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cGMP Peptide
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  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C12H22N2O5S
M.W/Mr.
306.38

Boc-D-Met-Gly-OH is a Boc-protected dipeptide acid featuring D-methionine and glycine in a defined stereochemical arrangement. As a protected amino acid derivative, it is commonly used as a building block for assembling peptide sequences where controlled N-terminus protection and a methionine-containing segment are required. The Boc carbamate provides an acid-labile N-terminal protection strategy that supports downstream peptide coupling workflows in research and pharmaceutical intermediate development.

1. Protected Dipeptide Building Block

Boc-D-Met-Gly-OH is used as a protected dipeptide building block in custom peptide synthesis workflows where a D-Met-Gly motif must be introduced with a Boc-protected N-terminus. Peptide chemists rely on this defined segment to improve sequence control during iterative coupling, particularly when preparing stereochemically specific peptide analogs, peptide standards, or intermediate fragments for longer constructs. The presence of methionine contributes a thioether side chain that is frequently retained through peptide assembly to enable subsequent functional studies or further derivatization at later stages.

2. Peptide Fragment Coupling

Boc-D-Met-Gly-OH serves as a convenient coupling partner for segment condensation strategies in both solution-phase and automated peptide synthesis development. Researchers developing peptide libraries or lead-optimization analogs often choose this format because the Boc protection supports consistent handling of the N-terminus during activation and coupling steps, while the free carboxylic acid at the C-terminus enables productive formation of the next peptide bond. This makes the reagent particularly useful for preparing longer peptide intermediates where the D-configuration at the methionine position is required for conformational or stability-related structure-activity relationship studies.

3. Pharmaceutical Intermediate Development

Boc-D-Met-Gly-OH is frequently selected in medicinal chemistry and pharmaceutical intermediate development for the preparation of stereochemically defined peptide fragments that can be carried forward into larger synthetic sequences. Process-oriented teams value the protected dipeptide format because it provides a clear, isolable intermediate with a defined composition (D-Met-Gly) and a Boc-protected N-terminus, supporting reproducible downstream coupling operations. This product form is also commonly used when building blocks must be characterized and handled as discrete units prior to final assembly into advanced peptide candidates or reference materials for analytical method development.

4. Analytical Reference Peptide Segment

Boc-D-Met-Gly-OH is used as a reference segment in analytical workflows that require defined peptide composition, such as method development and characterization of peptide intermediates by LC-MS or related techniques. Because the reagent contains a stereochemically defined D-methionine residue and a glycine C-terminus, it can function as a practical standard for verifying retention behavior, fragmentation patterns, and identity of related synthetic mixtures during peptide process development. Laboratories that generate peptide intermediates for SAR studies often incorporate such protected dipeptide references to support confident assignment of intermediate structures throughout synthesis and purification scouting.

Size
5 g;25 g;
InChI
1S/C12H22N2O5S/c1-12(2,3)19-11(18)14-8(5-6-20-4)10(17)13-7-9(15)16/h8H,5-7H2,1-4H3,(H,13,17)(H,14,18)(H,15,16)/t8-/m1/s1
InChI Key
PEKPTLWQVLOJAJ-MRVPVSSYSA-N
Canonical SMILES
CC(C)(C)OC(=O)NC(CCSC)C(=O)NCC(=O)O

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