127043-32-7

Basic information

• Product Name: FMOC-D-ALA-ALDEHYDE
• Synonyms: FMOC-D-ALA-ALDEHYDE;(R)-(9H-fluoren-9-yl)methyl 1-oxopropan-2-ylcarbamate
• CAS NO: 127043-32-7
• Molecular Formula: C₁₈H₁₇NO₃
• Molecular Weight: 295.33
• Mol File: 127043-32-7.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: FMOC-D-ALA-ALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-ALA-ALDEHYDE(127043-32-7)
• EPA Substance Registry System: FMOC-D-ALA-ALDEHYDE(127043-32-7)

Safety Data

• Hazardous Substances Data: 127043-32-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical and Biotechnology Industries:
FMOC-D-ALA-ALDEHYDE is used as a reagent for the synthesis of peptide derivatives due to its ability to protect D-alanine and facilitate the formation of peptide bonds. Its selective deprotection under mild conditions and the presence of the aldehyde functional group make it an essential component in the development of new pharmaceutical compounds and biotechnological applications.
Used in Organic Synthesis:
FMOC-D-ALA-ALDEHYDE is used as a building block in the synthesis of complex organic molecules, leveraging its aldehyde functional group for the formation of various chemical bonds and its FMOC group for protecting the D-alanine during the synthesis process.
Used in Peptide Chemistry:
FMOC-D-ALA-ALDEHYDE is used as a key component in the assembly of peptides, where its protected D-alanine can be selectively deprotected to enable the formation of peptide bonds, contributing to the creation of bioactive peptides and peptide-based drugs.

Upstream product

• 202751-95-9 (R)-(9H-fluoren-9-yl)methyl 1-hydroxypropan-2-ylcarbamate 
• 35661-38-2 N-(9-fluorenylmethoxycarbonyl)-D-alanine 
• 382149-16-8 (R)-(9H-fluoren-9-yl)methyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate 
• 129288-35-3 (R)-4-Methyl-2,5-dioxo-oxazolidine-3-carboxylic acid 9H-fluoren-9-ylmethyl ester 

Downstream Products

• 758677-60-0 benzyl N-(2-Fmoc-amino-D-methylethyl)glycinate 
• 382149-39-5 {[2-(9H-fluoren-9-ylmethoxycarbonylamino)-propyl]-[(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-acetyl]-amino}-acetic acid benzyl ester 
• 1189357-57-0 benzyl (R)-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-(E)-2-pentenoate 
• 1311399-88-8 FmocNH-D-Ala-ψ[C3H3NO]-CO-NH Phe-COOMe 
• 1447194-96-8 benzyl 4-[(1R)-1-(N-fmoc)aminoethyl]-2-methyl-1,3-thiazole-5-carboxylate 

Relevant articles and documents

Rational Design and Synthesis of Right-Handed d -Sulfono-γ-AApeptide Helical Foldamers as Potent Inhibitors of Protein-Protein Interactions

Novel unprecedented helical foldamers have been effectively designed and synthesized. The homogeneous right-handed d-sulfono-γ-AApeptides represent a new generation of unnatural helical peptidomimetics, which have similar folding conformation to α-peptide

LEFT-HANDED GAMMA-PEPTIDE NUCLEIC ACIDS, METHODS OF SYNTHESIS AND USES THEREFOR

A method of making optically pure preparations of chiral γΡΝΑ (gamma peptide nucleic acid) monomers is provided. Nanostructures comprising chiral γΡΝΑ structures also are provided. Methods of amplifying and detecting specific nucleic acids, including in situ methods are provided as well as compositions and kits useful in those methods. Lastly, methods of converting nucleobase sequences from right-handed helical PNA, nucleic acid and nucleic acid analog structures to left-handed γΡΝΑ, and vice- versa, are provided.

Helical oligomers of thiazole-based γ-amino acids: Synthesis and structural studies

9-Helix: 4-Amino(methyl)-1,3-thiazole-5-carboxylic acids (ATCs) were synthesized as new γ-amino acid building blocks. The structures of various ATC oligomers were analyzed in solution by CD and NMR spectroscopy and in the solid state by X-ray crystallography. The ATC sequences adopted a well-defined 9-helix structure in the solid state and in aprotic and protic organic solvents as well as in aqueous solution. Copyright

Structure-affinity relationships of glutamine mimics incorporated into phosphopeptides targeted to the SH2 domain of signal transducer and activator of transcription 3

In cancer cells, signal transducer and activator of transcription 3 (Stat3) participates in aberrant growth, survival, angiogenesis, and invasion signals and is a validated target for anticancer drug design. We are targeting its SH2 domain to prevent docking to cytokine and growth factor receptors and subsequent signaling. One of the important elements of the recognition sequence, pTyr-Xxx-Xxx-Gln, is glutamine. We incorporated novel Gln mimics into a lead peptide, pCinn-Leu-Pro-Gln-NHBn, and found that a linear, unconstrained side chain and carboxamide are necessary for high affinity, and the benzamide can be eliminated. Replacement of Gln-NHBn with (R)-4-aminopentanamide or 2-aminoethylurea produced inhibitors with equal or greater potency than that of the lead, as judged by fluorescence polarization (IC50 values were 110 and 130 nM, respectively). When Pro was replaced with cis-3,4- methanoproline, the glutamine mimic, (4R,5S)-4-amino-5-benzyloxyhexanamide resulted in an IC50 of 69 nM, the highest affinity Stat3 inhibitor reported to date. 2009 American Chemical Society.

Synthesis of chiral peptide nucleic acids using Fmoc chemistry

A Fmoc-based synthesis of chiral PNAs is described. Chiral monomer backbones were efficiently prepared by reductive amination of N-Fmoc-protected L,D-alaninals with glycine esters and the subsequent acylation of free amines with thymine-1-ylacetic acid. T

Synthesis of Chiral N-Protected α-Amino Aldehydes by Reduction of N-Protected N-Carboxyanhydrides (UNCAs)

A facile one step synthesis of a wide variety of N-protected (Boc, Z, Fmoc) α-amino aldehydes under mild conditions is described.Pure N-protected (Boc, Z, Fmoc) α-amino aldehydes were obtained in high yields by reduction of N-protected (Z, Boc, Fmoc)-N-ca