5191-80-0

Basic information

• Product Name: H-CYS(DPM)-OH
• Synonyms: H-CYS(DPM)-OH;CYSTEINE(DPM)-OH;S-DIPHENYLMETHYL-L-CYSTEINE;l-3-(diphenylmethylthio)alanine;(R)-S-Diphenylmethylcysteine;(R)-2-aMino-3-(benzhydrylthio)propanoic acid;NSC 86162;S-Benzhydryl-L-cysteine
• CAS NO: 5191-80-0
• Molecular Formula: C₁₆H₁₇NO₂S
• Molecular Weight: 287.38
• Mol File: 5191-80-0.mol
• Article Data: 3

Chemical Properties

• Melting Point: 206-207℃ (decomposition)
• Boiling Point: 455.5°Cat760mmHg
• Flash Point: 229.3°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 4.34E-09mmHg at 25°C
• Refractive Index: 1.63
• Storage Temp.: Store at RT.
• CAS DataBase Reference: H-CYS(DPM)-OH(CAS DataBase Reference)
• NIST Chemistry Reference: H-CYS(DPM)-OH(5191-80-0)
• EPA Substance Registry System: H-CYS(DPM)-OH(5191-80-0)

Safety Data

• Hazardous Substances Data: 5191-80-0(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

The S-diphenylmethyl group is one of the most effective S-protecting groups for cysteine.

InChI:InChI=1/C16H17NO2S/c17-14(16(18)19)11-20-15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,14-15H,11,17H2,(H,18,19)

Upstream product

• 52-89-1 l-cysteine hydrochloride 
• 90-99-3 diphenylchloromethane 
• 91-01-0 1,1-Diphenylmethanol 
• 52-90-4 L-Cysteine 

Downstream Products

• 58885-37-3 S-benzhydryl-L-cysteine methyl ester 
• 94932-39-5 N-Formyl-S-diphenyl-methyl-L-cystein 
• 21947-97-7 N-(t-butyloxycarbonyl)-S-(diphenylmethyl)-L-cysteine 
• 19595-55-2 S-Diphenylmethyl-N-acetyl-L-cystein 
• 53957-20-3 N-Carbobenzoxy-S-diphenyl-methyl-L-cystein 
• 56-89-3 L-cystine 
• 194019-37-9 [N-(5-methyloxycarbonyl)pentyl]-(S-benzhydryl-L-cysteine) 
• 790244-48-3 (S)-5-((R)-2-Benzhydrylsulfanyl-1-carboxy-ethylcarbamoyl)-2-tert-butoxycarbonylamino-pentanoic acid 4-methoxy-benzyl ester 
• 194019-38-0 [N-(5-methyloxycarbonyl)pentyl]-(S-benzhydryl-L-cysteinyl)-D-valine tert-butyl ester 
• 113787-88-5 S-(diphenylmethyl)-L-cysteinyl-D-valine benzhydryl ester 
• 113787-89-6 iodoacetyl-L-(S-diphenylmethyl)cysteinyl-D-valine benzhydryl ester 
• 113787-87-4 N-(t-butyloxycarbonyl)-S-(diphenylmethyl)-L-cysteinyl-D-valine benzhydryl ester 
• 113787-91-0 2-<3-(3-trifluoromethyl-3H-diazirin-3-yl)phenoxy>acetyl-L-(S-diphenylmethyl)cysteinyl-D-valine 
• 113787-90-9 2-<3-(3-trifluoromethyl-3H-diazirin-3-yl)phenoxy>acetyl-L-(S-diphenylmethyl)cysteinyl-D-valine benzhydryl ester 

Relevant articles and documents

Crystallographic studies on the reaction of isopenicillin N synthase with an unsaturated substrate analogue

Isopenicillin N synthase (IPNS) catalyses conversion of the linear tripeptie δ-(L-α-aminoadipoyl)-L-cysteinyl-D-valine (ACV) to isopenicillin N (IPN), the central step in biosynthesis of the β-lactam antibiotics. The unsaturated substrate analogue δ-(L-α-aminoadipoyl)-L-cysteinyl-D-vinylglycine (ACvG) has previously been incubated with IPNS and a single product was isolated, a 2-α-hydroxymethyl isopenicillin N (HMPen), formed via a monooxygenase mode of reactivity. ACvG has now been crystallised with IPNS and the structure of the anaerobic IPNS:Fe(II):ACvG complex determined to 1.15 A resolution. Furthermore, by exposing the anaerobically grown crystals to high-pressure oxygen gas, a structure corresponding to the bicyclic product HMPen has been obtained at 1.60 A resolution. In light of these and other IPNS structures, and recent developments with related dioxygenases, the [2 + 2] cycloaddition mechanism for HMPen formation from ACvG has been revised, and a stepwise radical mechanism is proposed. This revised mechanism remains consistent with the observed stereospecificity of the transformation, but fits better with apparent constraints on the coordination geometry around the active site iron atom.

Sulfide derivatives of cysteine.

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