Boc-Ala-Gly-OH

Boc-Ala-Gly-OH is a protected peptide-related intermediate consisting of an alanine-glycine dipeptide motif in which the N-terminus is protected as a Boc (tert-butoxycarbonyl) carbamate. The molecule bears a free C-terminal carboxylic acid (-COOH) and an unprotected glycine side chain (-CH2-), while the Boc group controls chemoselectivity by masking the N-terminus to suppress undesired amide-bond formation at that site during stepwise coupling. Boc-Ala-Gly-OH is used in peptide synthesis workflows to assemble longer peptide chains via controlled formation of new peptide bonds, supporting sequential elaboration of the C-terminus in solution-phase or solid-phase strategies.

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

CAT No: CP26958

CAS No:28782-78-7

Synonyms/Alias:28782-78-7; BOC-Ala-Gly; BOC-ALA-GLY-OH; (S)-2-(2-((tert-Butoxycarbonyl)amino)propanamido)acetic acid; n-(tert-butoxycarbonyl)-l-alanylglycine; AC1L4UAI; N-[N-[(1,1-Dimethylethoxy)carbonyl]-L-alanyl]glycine; AC1Q5XN8; SCHEMBL8536884; MolPort-006-125-650; ZINC2556536; AR-1K0239; AKOS015914167; AJ-39922; AK-48102; N-(N-tert-butoxycarbonyl-alanyl)-glycine; KB-300021; ST2402764; 2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]acetic acid; Glycine, N-[(1,1-dimethylethoxy)carbonyl]-L-alanyl-; (tert-butoxycarbonyl)-L-alanylglycine; MFCD00235759; Boc-Ala-Gly-OH, AldrichCPR; HY-W019684; DA-51279; DS-14559; CS-0030797; NS00047500; (S)-2-(2-(tert-butoxycarbonylamino)propanamido)acetic acid; [(2S)-2-[(tert-Butoxycarbonyl)amino]propanamido]acetic acid (Boc-L-Ala-Gly-OH)

Custom Peptide Synthesis
cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C10H18N2O5
M.W/Mr.
246.26
Sequence
One Letter Code:AG

Boc-Ala-Gly-OH is a protected dipeptide acid featuring an N-terminal Boc (tert-butoxycarbonyl) group, combining alanine and glycine in a short peptide building block format. This structure provides a pre-assembled peptide motif with a carboxylic acid at the C-terminus, making it well suited for downstream peptide coupling strategies and intermediate synthesis where controlled amide formation is required.

1. Peptide Segment Coupling

Boc-Ala-Gly-OH is used by peptide synthesis groups as a dipeptide segment for constructing longer peptide chains via amide bond formation at the C-terminus. Because the N-terminus is protected as Boc, the molecule can be handled as a defined coupling unit while minimizing undesired side reactions during fragment assembly. Researchers in custom peptide manufacturing and peptide chemistry laboratories commonly employ this type of protected dipeptide building block to streamline synthesis of sequences containing the Ala-Gly motif and to improve reproducibility across batch preparations.

2. Solution-Phase Peptide Assembly

Boc-Ala-Gly-OH fits well into solution-phase peptide synthesis workflows where chemists build peptide targets by sequential coupling of protected fragments. The presence of the free C-terminal carboxylic acid functionality supports its use as a coupling partner in iterative assembly strategies, while the Boc protection pattern helps control reactivity during the early stages of chain growth. This makes the reagent practical for medicinal chemistry teams preparing peptide-based leads, peptidomimetics, or peptide intermediates that require precise sequence definition before subsequent functionalization or purification.

3. Pharmaceutical Intermediate Development

Boc-Ala-Gly-OH is frequently selected as a stable, isolable intermediate for manufacturing routes that require incorporation of an Ala-Gly unit into a larger protected peptide framework. Process development chemists and intermediate manufacturers value short, protected peptide acids because they can be standardized as feedstocks for later coupling steps, reducing variability associated with in situ formation of peptide fragments. In this context, the Boc-protected N-terminus and carboxylic acid end support predictable downstream transformations toward more complex peptide derivatives used in research and development pipelines.

4. Analytical Reference Building Block

Boc-Ala-Gly-OH is also used in analytical method development and characterization workflows as a defined peptide standard or reference material for verifying coupling performance and monitoring fragment integrity. Laboratories developing LC-MS or HPLC-based assays for peptide synthesis commonly rely on well-defined protected peptide acids to benchmark retention behavior and mass spectral signatures of expected intermediates. This application is especially relevant when confirming that the Ala-Gly motif has been introduced correctly during peptide assembly prior to progressing to later synthetic stages.

Size
5 g;25 g;
InChI
1S/C10H18N2O5/c1-6(8(15)11-5-7(13)14)12-9(16)17-10(2,3)4/h6H,5H2,1-4H3,(H,11,15)(H,12,16)(H,13,14)/t6-/m0/s1
InChI Key
PBGVVLQMNSPMKN-LURJTMIESA-N
Canonical SMILES
CC(C(=O)NCC(=O)O)NC(=O)OC(C)(C)C

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