Boc-Ala-Gly-OSu

Boc-Ala-Gly-OSu is a protected peptide-related intermediate consisting of an alanine-glycine dipeptide framework in which the alanine amino group is protected as a Boc (tert-butoxycarbonyl) carbamate and the terminal carboxyl group is converted to an N-hydroxysuccinimide (OSu) ester. The molecule contains an N-Boc-protected amide linkage between the alanine and glycine residues, a free glycine side-chain functionality consistent with glycine (no additional side-chain substituent), and an OSu-activated carboxyl group that can undergo acyl transfer to form amide bonds under appropriate conditions. Boc-Ala-Gly-OSu is used in peptide synthesis and bioconjugation workflows as an activated carboxylate building block for coupling reactions that generate peptide or amide-linked products while the Boc group helps control chemoselectivity at the amino terminus.

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

CAT No: CP27427

CAS No:74535-75-4

Synonyms/Alias:BOC-ALA-GLY-OSU;74535-75-4;ZINC2560849;AM001969;2,5-DIOXOPYRROLIDIN-1-YL2-[(2S)-2-[(TERT-BUTOXYCARBONYL)AMINO]PROPANAMIDO]ACETATE

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cGMP Peptide
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  • Drug master files (DMF) filing
M.F/Formula
C14H21N3O7
M.W/Mr.
343.34

Boc-Ala-Gly-OSu is a Boc-protected peptide ester in which alanine and glycine are preassembled as an amino-acid dipeptide unit terminated as an N-hydroxysuccinimide (OSu) ester. This activated ester format is widely used to drive amide bond formation under mild conditions, making the reagent valuable for peptide coupling, fragment assembly, and preparation of peptide-linked conjugates. The Boc group provides a protected N-terminus that helps control reactivity during downstream coupling and intermediate handling.

1. Peptide Coupling Reagent

Boc-Ala-Gly-OSu is used as an activated dipeptide building block for coupling reactions where formation of a new amide bond is required with an amine-containing partner, such as in custom peptide synthesis and fragment condensation workflows. Researchers in peptide chemistry and contract peptide manufacturing often select OSu-activated peptide esters to promote efficient coupling while maintaining compatibility with standard peptide intermediate handling. The preassembled Ala-Gly sequence supports rapid assembly of longer peptide targets and helps streamline library synthesis where consistent dipeptide units are needed.

2. Peptide Fragment Condensation

Boc-Ala-Gly-OSu serves as a practical intermediate for constructing peptide fragments in both solution-phase and stepwise assembly strategies, particularly when the dipeptide motif must be introduced as a defined, protected unit. Medicinal chemistry groups developing peptidomimetic or peptide-based leads frequently rely on activated peptide esters to couple peptide fragments to additional residues or functionalized side chains, enabling controlled growth of the sequence. The combination of Boc protection on the N-terminus and OSu activation at the C-terminus supports predictable downstream processing and helps maintain the integrity of the assembled fragment during iterative synthesis.

3. Amide-Linked Bioconjugate Building

Boc-Ala-Gly-OSu is commonly employed to generate amide linkages between peptide fragments and amine-bearing biomolecules or scaffold materials, supporting the preparation of peptide-conjugated constructs used in chemical biology. Bioconjugation workflows often use OSu-activated esters to couple to primary amines under conditions that preserve sensitive functional groups on the partner molecule. This makes Boc-Ala-Gly-OSu a useful reagent when a defined Ala-Gly peptide handle is needed to attach targeting motifs, affinity tags, or carrier-like structures through a stable amide bond.

4. Pharmaceutical Intermediate Assembly

Boc-Ala-Gly-OSu is also used in pharmaceutical intermediate development where defined peptide units must be incorporated into larger synthetic sequences with controlled reactivity and reliable coupling performance. Process development chemists and industrial R&D teams often value OSu-activated peptide esters as intermediates that can translate well from small-scale synthesis to scale-up planning for peptide-containing intermediates. The reagent's protected dipeptide structure supports its role as a modular building block in the preparation of more complex, sequence-defined intermediates for downstream manufacturing steps.

Size
5 g;25 g;
InChI
1S/C14H21N3O7/c1-8(16-13(22)23-14(2,3)4)12(21)15-7-11(20)24-17-9(18)5-6-10(17)19/h8H,5-7H2,1-4H3,(H,15,21)(H,16,22)/t8-/m0/s1
InChI Key
WONRGZBZQQESHS-QMMMGPOBSA-N
Canonical SMILES
CC(C(=O)NCC(=O)ON1C(=O)CCC1=O)NC(=O)OC(C)(C)C

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