Fmoc-L-NptGly-OH is an Fmoc-protected amino acid derivative featuring an L-configured glycine core bearing an Npt (pentylthio) substituent on the amino nitrogen, classifying it as a substituted glycine building block for peptide chemistry. The molecule contains a free carboxylic acid (-COOH) for coupling and an Fmoc carbamate that masks the α-amino functionality, while the Npt group provides a sulfur-containing side-chain substituent that can be used as a chemical handle in derivative formation or post-synthetic modification. In synthetic workflows such as stepwise peptide assembly, the protected α-amino group supports controlled chemoselectivity during chain elongation, and the Npt-bearing glycine residue supports preparation of labeled or functionally modified peptide materials for structure-activity studies and analytical method development.
CAT No: CP25344
CAS No:139551-74-9
Synonyms/Alias:139551-74-9;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4,4-dimethylpentanoic acid;Fmoc-beta-t-butyl-L-alanine;Fmoc-Ala(tBu)-OH;L-Leucine, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-methyl-;FMOC-T-BUTYL-L-ALANINE;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-4,4-dimethylpentanoic acid;Fmoc-neopentylglycine;MFCD00671389;(2S)-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-4,4-dimethylpentanoic acid;Fmoc-L-tBuAla-OH;Fmoc-b-tBu-Ala-OH;Fmoc-neopentylglycine; (S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-4,4-dimethylpentanoic Acid; Fmoc-Ala(tBu)-OH; N-(9-Fluorenylmethyloxycarbonyl)-neopentylglycine;Fmoc-b-tBu-L-Ala-OH;N-Fmoc-4-methyl-L-leucine;FMOC-gamma-methyl-L-leucine;SCHEMBL2367428;RPLVCXKSSXJFDS-IBGZPJMESA-N;Fmoc-t-butyl-L-alanine, AldrichCPR;AKOS015837134;AKOS015907934;CS-W007051;FF49789;DS-16274;EN300-6474828;L-Leucine,N-[(9H-fluoren-9-ylmethoxy)carbonyl]-4-methyl-;N-(9-Fluorenylmethyloxycarbonyl)-neopentylglycine (Fmoc-L-NptGly-OH);(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4,4-dimethylpentanoic acid;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4,4-dimethylpentanoic acid;810-059-1;
Chemical Name:N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-neopentylglycine
Fmoc-L-NptGly-OH is an Fmoc-protected L-amino acid derivative built on an NptGly (N-protected glycine) motif, providing an N-Fmoc group for orthogonal base-mediated deprotection during peptide assembly. The molecule contains a free carboxylic acid functionality that participates in standard peptide coupling chemistry, while the chiral information is defined by the L-configuration at the amino acid stereocenter associated with the glycine-derived scaffold. The Fmoc carbamate and the Npt protecting group modulate nucleophilicity and chemoselectivity, enabling controlled exposure of the reactive amine only when desired. The resulting protected amino acid intermediate is designed for compatibility with solid-phase peptide synthesis workflows and downstream synthesis of peptidic and peptidomimetic structures.
1. Peptide Synthesis
Fmoc-L-NptGly-OH is used in peptide synthesis as an Fmoc-protected amino acid building block for stepwise chain elongation, where the Fmoc group supports base-labile deprotection to reveal the coupling-ready amine. The free carboxylic acid enables amide bond formation under common peptide coupling conditions, while the Npt-protection strategy suppresses side reactions from the amino functionality during activation and coupling. The defined L-configuration and protected amine profile support stereochemically consistent incorporation into peptides and peptide fragments. The compound can be employed to prepare glycine-containing sequences, including those requiring orthogonal protection to preserve other functional groups in the growing peptide.
2. Protected Amino Acid Chemistry
Fmoc-L-NptGly-OH is suitable for protected amino acid synthesis and intermediate preparation where orthogonal protection is required to manage reactivity across multiple functional groups. The Fmoc carbamate provides a robust N-protection handle that can be removed without directly disturbing the carboxylic acid, supporting controlled generation of a free amine for subsequent derivatization or coupling. The Npt group further tunes chemoselectivity by reducing undesired nucleophilicity during intermediate handling, activation, and purification. The resulting protected amino acid derivative can be applied as a building block in synthetic planning for peptide-like scaffolds, including protected fragment assembly and sequential deprotection strategies.
3. Peptidomimetics Construction
Fmoc-L-NptGly-OH can be incorporated into peptidomimetic construction workflows that require well-defined amide connectivity and controlled functional group exposure. The amino acid backbone and carboxylic acid functionality support conversion into amide-linked intermediates that can be further transformed into constrained analogs, backbone-modified linkages, or terminally functionalized fragments. The protected amine architecture helps maintain compatibility with chemoselective transformations, enabling downstream derivatization after peptide assembly or fragment coupling. The compound thereby serves as a chiral amino acid intermediate for generating peptide analogs used in molecular design and structure-focused synthetic libraries.
4. Chemical Biology Labeling
Fmoc-L-NptGly-OH is applicable to chemical biology and biomolecule modification programs where peptide fragments containing defined protecting-group patterns are needed for conjugation-ready intermediates. The Fmoc-protected amine and free carboxylic acid allow incorporation into short peptides or peptide tags that can later be deprotected and coupled to reactive handles such as activated esters, aldehyde-derived linkers, or maleimide-type electrophiles depending on the chosen conjugation chemistry. The orthogonal protection strategy supports sequential functional group unveiling, which can be important when building multifunctional probes from amino acid derivatives. The compound can be used to generate labeled peptide constructs and standardized intermediates for analytical characterization of conjugates.
5. Pharmaceutical Manufacturing
Fmoc-L-NptGly-OH is relevant to pharmaceutical manufacturing and fine chemical synthesis routes that rely on reproducible peptide building blocks for process-scale solid-phase or solution-phase assembly of peptide intermediates. The Fmoc protection system supports controlled deprotection steps that can be integrated into manufacturing workflows to minimize side reactions from unprotected amines during coupling operations. The presence of a free carboxylic acid ensures compatibility with established peptide coupling methodologies used to manufacture peptide-grade intermediates and defined fragments. The compound can therefore serve as a process chemistry intermediate for producing peptide components that feed into larger synthesis campaigns, including those requiring protected amino acid handling discipline and predictable downstream transformations.
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