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| Product Name | Fmoc-Gly-OH |
|---|---|
| Synonyms | Fmoc-glycine; N-Fmoc-glycine |
| Catalog No. | AS1216 |
| CAS Number | 29022-11-5 |
| Molecular Formula | C17H15NO4 |
| Molecular Weight | 297.31 g/mol |
| SMILES | OC(=O)CNC(=O)OCC1c2ccccc2-c3ccccc13 |
| Storage Temperature | Cool, dry place (≤25°C) |
| Appearance | White powder |
| Melting Point | 165–185°C |
| Chirality | Achiral |
| Functional Groups | Fmoc-protected amino group; free carboxylic acid |
| Primary Application | Fmoc solid-phase peptide synthesis (SPPS) |
Product Overview
Fmoc-Gly-OH is the Fmoc-protected form of glycine and one of the most fundamental building blocks in peptide synthesis.
Unlike most proteinogenic amino acids, glycine has no side-chain carbon beyond hydrogen and therefore contains no stereogenic α-carbon. As a result, glycine does not present the conventional α-carbon racemization issue encountered with chiral amino acids.
No side-chain protecting group is required.
This simple structure makes Fmoc-Gly-OH widely applicable in:
conventional peptide synthesis
flexible peptide linkers
glycine-rich sequences
peptide libraries
spacer design
cyclic and modified peptides
Applications in Peptide Synthesis
| Application | Role of Fmoc-Gly-OH |
|---|---|
| Fmoc-SPPS | Standard glycine building block |
| Flexible Linkers | Introduces minimal steric bulk and high backbone flexibility |
| Gly-Rich Peptides | Supports sequences containing repeated glycine residues |
| Peptide Conjugates | Can be incorporated into spacer and linker regions |
| Peptide Libraries | Common residue in sequence-diverse libraries |
| SAR Studies | Used to reduce side-chain bulk at defined positions |
| Custom Peptide Synthesis | Suitable for routine and complex peptide projects |
Fmoc-Gly-OH in Fmoc-SPPS
Fmoc-Gly-OH requires only α-amino protection because glycine has no functional side chain requiring protection.
The free carboxyl group is activated and coupled to the resin-bound amine. After incorporation, Fmoc is removed under standard basic conditions to expose the amino terminus for further chain elongation.
Its lack of side-chain protection makes Fmoc-Gly-OH chemically simpler than many protected amino-acid building blocks.
Explore the broader family of Standard Fmoc-Amino Acids.
Why Glycine Is Chemically Different
Glycine is unique among the 20 standard proteinogenic amino acids because its side chain is simply hydrogen.
This produces two important consequences.
First, glycine is achiral, meaning conventional L/D stereochemical designation does not apply.
Second, glycine provides greater backbone conformational freedom than most amino acids.
Depending on sequence context, this can be useful for:
flexible linkers
turns and loops
reducing local steric crowding
connecting functional peptide domains
allowing conformational rearrangement around binding regions
However, additional flexibility is not always beneficial. In a bioactive peptide, replacing a conformationally restricted residue with glycine may increase entropy and reduce the population of a binding-competent conformation.
Alan Scientific practical view: Gly substitution is therefore not merely a “smaller residue” substitution. It can materially change peptide conformational behavior.
Glycine as a Peptide Linker and Spacer
Glycine is frequently combined with residues such as serine to construct flexible linker sequences.
Its small size makes it useful where the objective is to separate two functional regions without introducing a bulky or strongly interacting side chain.
Examples include:
peptide–protein linkers
multifunctional peptide constructs
fluorescent peptide designs
conjugated peptides
cyclic peptide linker regions
For these applications, linker length should be optimized according to the required geometry rather than simply adding multiple Gly residues without structural rationale.
For projects involving linker design or modification, see Custom Peptide Synthesis.
Analytical Considerations
Because glycine contains no stereocenter, chiral purity is generally not a meaningful specification for Fmoc-Gly-OH in the same way that D-isomer content is for L-amino-acid building blocks.
More relevant quality parameters include:
chemical purity
identity
water content
residual starting materials
Fmoc-related impurities
coupling performance
Sigma currently specifies Fmoc-Gly-OH for peptide synthesis and reports a reference melting range around 174–178°C, which lies within Alan Scientific's broader 165–185°C product range.
Product Documents
A Safety Data Sheet (SDS / MSDS) is available for this product to support laboratory handling, storage and safety assessment.
Related Technical Resources
Learn more in Solid-Phase Peptide Synthesis (SPPS): A Practical Guide.
Explore Amino Acids & Peptide Building Blocks.
Browse Standard Fmoc-Amino Acids.
For complete peptide projects, see Custom Peptide Synthesis.
Why Source Peptide Building Blocks from Alan Scientific?
Alan Scientific supplies Fmoc-protected amino acids and specialized peptide building blocks for research peptide synthesis, supported by flexible ordering and peptide synthesis expertise.
Research Use Only