157355-80-1

Basic information

• Product Name: FMOC-D-CYS-OH
• Synonyms: FMOC-D-CYS-OH;N-ALPHA-FMOC-D-CYSTEINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-D-CYSTEINE;Fmoc-D-Cys-OH·H2O;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-cysteine;(9H-Fluoren-9-yl)MethOxy]Carbonyl D-Cys-OH·H2O;(S)-2-((((9H-FLUOREN-9-YL)METHOXY)CARBONYL)AMINO)-3-MERCAPTOPROPANOIC ACID
• CAS NO: 157355-80-1
• Molecular Formula: C₁₈H₁₇NO₄S
• Molecular Weight: 343.4
• Mol File: 157355-80-1.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 574.4±50.0 °C(Predicted)
• Appearance: /
• Density: 1.337±0.06 g/cm3(Predicted)
• PKA: 3.45±0.10(Predicted)
• CAS DataBase Reference: FMOC-D-CYS-OH(CAS DataBase Reference)
• NIST Chemistry Reference: FMOC-D-CYS-OH(157355-80-1)
• EPA Substance Registry System: FMOC-D-CYS-OH(157355-80-1)

Safety Data

• Hazardous Substances Data: 157355-80-1(Hazardous Substances Data)

Usage

Uses

N-Fmoc-D-cysteine is an N-Fmoc-protected form of D-Cysteine (C995020). D-Cysteine is a strong inhibitor of Escherichia coli growth and also functions to provide inorganic sulfates for the sulfation of xenobiotics. D-Cysteine is a non-physiological isomer of L-Cysteine (C995000), and is not involved in protein or glutathione synthesis.

Upstream product

• 167015-11-4 Fmoc-D-Cys(Trt)-OH 

Relevant articles and documents

Solid-phase synthesis of 3,5-disubstituted 2,3-dihydro-1,5- benzothiazepin-4(5H)-ones

A solid-phase route affording novel 3,5-disubstituted 1,5- benzothiazepin-4(5H)-ones in optically pure form has been enabled. S(N)Ar reaction of polymer-bound 4-fluoro-3-nitrobenzoic acid, 12, with L-Fmoc- cysteine, L-13, under basic conditions, followed by tin(II) chloride mediated nitro group reduction, furnished the primary aniline 15. Reductive alkylation of 15 to the corresponding secondary anilines 17 was shown to be feasible for a wide range of aldehydes, using an optimized solvent system composed of CH(OMe)3, DMF, MeOH, and HOAc, with NaCNBH3 as the reducing agent. In cases of enolizable aldehydes, benzotriazole was found to be a beneficial additive for the suppression of side-products due to imine-enamine tautomerization. Subsequent cyclization of the secondary anilines 17 using DIC in apolar solvents furnished the corresponding N(5)-alkylated 1,5-benzothiazepin-4- ones 19. Following Fmoc removal from 19, the primary amino group was finally reacted with carboxylic acids, isocyanates, sulfonyl chlorides, or aldehydes to afford the respective amides 32, ureas 33, sulfonamides 34, or secondary amines 35. Performing the synthesis with the D-form of Fmoc-cysteine, D-13, resulted in the corresponding antipodal products, with no detectable scrambling at C(3). The solid-phase assembly of 1,5-benzothiazepin-4-ones was also shown to be compatible with chemical encoding based on dialkylamine tags, enabling the construction of large combinatorial libraries of the title compounds.

A compound and its preparation process and method for producing a polypeptide using the same

The invention discloses a compound, a preparation method thereof and a method for preparing a polypeptide by virtue of the compound. The compound has the structure specified in the description, wherein the N-terminal cysteine of the polypeptide can be protected by virtue of the compound, thus shielding the activity of the N-terminal cysteine, then connection for more (greater than or equal to 3) polypeptide segments can be realized when the polypeptide segments are connected to prepare proteins, i.e., separation and purification treatment is not needed after every two polypeptide segments are connected, and connection with the next polypeptide segment can be directly carried out after the shielding is removed.