198543-96-3

Basic information

• Product Name: FMOC-D-CHG-OH
• Synonyms: N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-D-CYCLOHEXYLGLYCINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-D-CYCLOHEXYLGLYCINE;FMOC-D-CHG-OH;FMOC-D-CYCLOHEXYLGLYCINE;FMOC-D-ALPHA-CYCLOHEXYLGLYCINE;FMOC-CYCLOHEXYL-D-GLYCINE;FMOC-CYCLOHEXYL-D-GLY-OH;FMOC-D-2-CYCLOHEXYLGLYCINE
• CAS NO: 198543-96-3
• Molecular Formula: C23H25NO4
• Molecular Weight: 379.45
• Product Categories: Amino Acids;Peptide
• Mol File: 198543-96-3.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 602.9±38.0 °C(Predicted)
• Appearance: /Solid
• Density: 1.238
• Storage Temp.: -15°C
• PKA: 3.89±0.10(Predicted)
• CAS DataBase Reference: FMOC-D-CHG-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-CHG-OH(198543-96-3)
• EPA Substance Registry System: FMOC-D-CHG-OH(198543-96-3)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 198543-96-3(Hazardous Substances Data)

Usage

General Description

Fmoc-D-Chg-OH is a scientific term for a chemical compound often used in biochemical research. It stands for fluorenylmethyloxycarbonyl-D-cyclohexylglycine, a derivative of the amino acid glycine. Its structure contains an Fmoc group, which serves as protection for the amine during peptide synthesis. Fmoc-D-Chg-OH is utilized in the preparation of peptides, proteins and other organic compounds with its main application being solid-phase peptide synthesis. As an essential component in scientific research, it is typically synthesized in specialized laboratories under controlled conditions.

Upstream product

• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 14328-51-9 (2S)-amino(cyclohexyl)ethanoic acid 
• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 

Relevant articles and documents

Fungal Dioxygenase AsqJ Is Promiscuous and Bimodal: Substrate-Directed Formation of Quinolones versus Quinazolinones

Previous studies showed that the FeII/α-ketoglutarate dependent dioxygenase AsqJ induces a skeletal rearrangement in viridicatin biosynthesis in Aspergillus nidulans, generating a quinolone scaffold from benzo[1,4]diazepine-2,5-dione substrates. We report that AsqJ catalyzes an additional, entirely different reaction, simply by a change in substituent in the benzodiazepinedione substrate. This new mechanism is established by substrate screening, application of functional probes, and computational analysis. AsqJ excises H2CO from the heterocyclic ring structure of suitable benzo[1,4]diazepine-2,5-dione substrates to generate quinazolinones. This novel AsqJ catalysis pathway is governed by a single substituent within the complex substrate. This unique substrate-directed reactivity of AsqJ enables the targeted biocatalytic generation of either quinolones or quinazolinones, two alkaloid frameworks of exceptional biomedical relevance.

Total Synthesis and Biological Evaluation of Natural and Designed Tubulysins

A streamlined total synthesis of N14-desacetoxytubulysin H (Tb1) based on a C-H activation strategy and a short total synthesis of pretubulysin D (PTb-D43) are described. Applications of the developed synthetic strategies and technologies to the synthesis of a series of tubulysin analogues (Tb2-Tb41 and PTb-D42) are also reported. Biological evaluation of the synthesized compounds against an array of cancer cells revealed a number of novel analogues (e.g., Tb14), some with exceptional potencies against certain cell lines [e.g., Tb32 with IC50 = 12 pM against MES SA (uterine sarcoma) cell line and 2 pM against HEK 293T (human embryonic kidney) cell line], and a set of valuable structure-activity relationships. The highly potent cytotoxic compounds discovered in this study are highly desirable as payloads for antibody-drug conjugates and other drug delivery systems for personalized targeted cancer chemotherapies.