Z-Glu-Gly-OH: Properties, Uses & Handling FAQ
Z-Glu-Gly-OH: Properties, Uses & Handling FAQ
Z-Glu-Gly-OH is a benzyloxycarbonyl (Z/Cbz)-protected dipeptide consisting of glutamic acid and glycine, widely used as a building block in solution- and solid-phase peptide synthesis.
- Chemical Name
- N-Benzyloxycarbonyl-L-glutamyl-glycine (Z-Glu-Gly-OH)
- SKU / Catalog Number
- Z1303226
- Protecting Group
- Z (Cbz, benzyloxycarbonyl) on the α-amine of glutamic acid
- C-terminus Status
- Free carboxylic acid (OH), suitable for further coupling reactions
- Primary Application
- Building block for peptide synthesis; substrate in protease research
- Supplier
- Aladdin Scientific (Z1303226)
What Is Z-Glu-Gly-OH and How Is It Structured?
Z-Glu-Gly-OH is a dipeptide derivative in which the alpha-amino group of L-glutamic acid is protected by a benzyloxycarbonyl (Z or Cbz) group, and the C-terminus of glycine bears a free carboxylic acid. The full systematic description is N-Cbz-L-glutamyl-glycine.
The Z (Cbz) protecting group is one of the most classical and widely used amine-protecting groups in peptide chemistry. It is stable under mildly acidic and basic conditions but is cleanly removed by catalytic hydrogenolysis (e.g., H₂/Pd-C) or by treatment with strong acids such as HBr/AcOH. This orthogonal deprotection profile makes Z-Glu-Gly-OH highly versatile for multi-step synthesis strategies.
The free C-terminal carboxylic acid allows direct activation for coupling to the next amino acid or resin, making this compound a ready-to-use building block without additional modification at that terminus.
What Are the Typical Research Applications of Z-Glu-Gly-OH?
Z-Glu-Gly-OH serves several roles in biochemical and chemical research:
- Peptide synthesis building block: It provides a pre-assembled Glu-Gly dipeptide unit with a stable N-terminal protecting group, simplifying the synthesis of longer peptides containing this sequence.
- Protease substrate preparation: Glutamate- and glycine-containing sequences are found in many biologically relevant peptide substrates. Z-protected dipeptides are frequently used as precursors to chromogenic or fluorogenic substrates for enzyme kinetics and inhibitor screening assays.
- Structure–activity relationship (SAR) studies: Researchers incorporate Z-Glu-Gly units into peptide analogs to probe the binding requirements of proteases, peptidases, and receptors.
- Model compound for optimization: The well-defined structure allows chemists to optimize coupling conditions, racemization suppression, and deprotection protocols before applying them to more complex targets.
Solubility, Storage, and Handling Recommendations
Solubility: Z-protected dipeptides such as Z-Glu-Gly-OH are typically soluble in polar aprotic solvents including DMF and DMSO, as well as in mixtures of ethyl acetate and methanol. Aqueous solubility is generally limited at neutral pH but may improve under mildly basic conditions due to ionization of the carboxylic acid groups. Researchers should prepare stock solutions fresh or verify stability over time.
Storage: Store the compound in a cool, dry environment, protected from light and moisture. A temperature of 2–8 °C or −20 °C is commonly recommended for long-term storage of Z-protected peptide derivatives to minimize hydrolysis and oxidation. Always reseal containers under inert gas (nitrogen or argon) after use.
Handling: Use standard laboratory personal protective equipment (PPE) including gloves, lab coat, and eye protection. Although Z-Glu-Gly-OH is not classified as acutely hazardous, follow your institution's chemical hygiene plan. Consult the Safety Data Sheet (SDS) provided by Aladdin Scientific for product-specific hazard information.
Note: Specific verified solubility data and confirmed storage temperature for catalog item Z1303226 should be confirmed from the product SDS or Certificate of Analysis (CoA).
Purity, Quality, and Specification Considerations
For peptide synthesis applications, reagent purity is critical because impurities in building blocks can lead to deletion sequences, difficult purifications, and low overall yields. When ordering Z-Glu-Gly-OH (SKU Z1303226) from Aladdin Scientific, researchers should request or download the Certificate of Analysis (CoA) for the specific lot, which will list:
- Purity (typically assessed by HPLC)
- Identity confirmation (NMR, MS, or IR)
- Optical rotation (to confirm stereochemical integrity of the L-Glu residue)
- Appearance and physical state
If a higher purity grade is required for sensitive biological assays, contact Aladdin Scientific's technical support team to discuss available grades or custom specifications.
Note: Specific purity values for lot Z1303226 are not reproduced here; please consult the current CoA available on the Aladdin Scientific website or request one from customer service.
Frequently asked questions
What does the 'Z' prefix in Z-Glu-Gly-OH stand for, and how is it removed?
The 'Z' (also written as Cbz) stands for benzyloxycarbonyl, a classical N-protecting group introduced onto the alpha-amine of glutamic acid. It is removed by catalytic hydrogenolysis using hydrogen gas over a palladium catalyst (H₂/Pd-C) or by treatment with strong acids such as HBr in acetic acid, releasing the free amine, toluene, and CO₂ as byproducts.
Is Z-Glu-Gly-OH compatible with solid-phase peptide synthesis (SPPS)?
Z-Glu-Gly-OH can be used in Boc-strategy SPPS workflows, where Z protection is orthogonal to the Boc groups used on the growing chain, since Z is removed by hydrogenolysis while Boc is removed by TFA. It is less common in Fmoc-strategy SPPS, where the standard deprotection step uses piperidine, which does not remove the Z group; researchers should carefully plan orthogonal deprotection schemes if incorporating Z-protected fragments into an Fmoc workflow.
How should I activate the C-terminal carboxylic acid of Z-Glu-Gly-OH for peptide coupling?
The free C-terminal carboxylic acid can be activated using standard peptide coupling reagents such as DCC (dicyclohexylcarbodiimide), EDC, HBTU, HATU, or PyBOP, typically in the presence of a base (e.g., DIPEA or NMM) and an additive such as HOBt or HOAt to suppress racemization. The choice of reagent and conditions should be optimized based on the specific coupling partner and scale of the reaction.
Does the glutamic acid in Z-Glu-Gly-OH carry side-chain protection?
Based on the compound name Z-Glu-Gly-OH, only the alpha-amine of glutamic acid is protected by the Z group; the glutamic acid side-chain carboxyl is indicated as free. Researchers requiring side-chain protection (e.g., OBzl or OtBu on the gamma-carboxyl) should consider alternative protected building blocks or introduce side-chain protection separately. Please verify this interpretation against the CoA and structure provided with lot Z1303226.
What solvents are recommended for dissolving Z-Glu-Gly-OH?
Z-protected dipeptides are generally soluble in polar aprotic solvents such as DMF and DMSO, and in mixed systems like ethyl acetate/methanol. Aqueous solubility at neutral pH may be limited; alkaline aqueous solutions may improve dissolution due to carboxylate formation. For precise solubility data specific to catalog item Z1303226, consult the Aladdin Scientific product page or CoA, as values may vary by lot.
References
- Bodanszky, M. Principles of Peptide Synthesis. Springer-Verlag, Berlin, 1984. (General reference for Z/Cbz protecting group chemistry and dipeptide building blocks.)
- Isidro-Llobet, A.; Álvarez, M.; Albericio, F. Amino Acid-Protecting Groups. Chemical Reviews, 2009, 109(6), 2455–2504. doi:10.1021/cr800323s
- Aladdin Scientific. Product Information: Z-Glu-Gly-OH, SKU Z1303226. Aladdin Scientific website (current lot CoA and SDS).
Products are supplied for research and development use only. Not for use in humans, animals, diagnosis, or therapy.
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