(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-amino-3-carbamoylpropanamido]-5-carbamimidamidopentanamido]-3-sulfanylpropanamido]-3-hydroxypropanamido]-4-carbamoylbutanamido]acetamido}-3-hydroxypropanamido]-3-sulfanylpropanamido]-3-(1H-indol-3-yl)propanamido]-3-carbamoylpropanoic acid

• ChemBase ID: 153796
• Molecular Formular: C44H67N17O16S2
• Molecular Mass: 1154.23708
• Monoisotopic Mass: 1153.43931115
• SMILES: c1ccc2c(c1)c(c[nH]2)C[C@@H](C(=O)N[C@@H](CC(=O)N)C(=O)O)NC(=O)[C@H](CS)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(=O)N)NC(=O)[C@H](CO)NC(=O)[C@H](CS)NC(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(=O)N)N
• Canonical SMILES: OC[C@@H](C(=O)N[C@H](C(=O)NCC(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CC(=O)N)Cc1c[nH]c2c1cccc2)CS)CO)CCC(=O)N)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@H](CC(=O)N)N)CCCNC(=N)N)CS
• InChI: InChI=1S/C44H67N17O16S2/c45-21(11-32(47)65)35(68)55-23(6-3-9-51-44(49)50)37(70)60-30(18-79)42(75)59-28(16-63)40(73)56-24(7-8-31(46)64)36(69)53-14-34(67)54-27(15-62)39(72)61-29(17-78)41(74)57-25(38(71)58-26(43(76)77)12-33(48)66)10-19-13-52-22-5-2-1-4-20(19)22/h1-2,4-5,13,21,23-30,52,62-63,78-79H,3,6-12,14-18,45H2,(H2,46,64)(H2,47,65)(H2,48,66)(H,53,69)(H,54,67)(H,55,68)(H,56,73)(H,57,74)(H,58,71)(H,59,75)(H,60,70)(H,61,72)(H,76,77)(H4,49,50,51)/t21-,23-,24-,25-,26-,27-,28-,29-,30-/m0/s1
• InChIKey: KEQZTNKTLNAKCM-XFPWREGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-amino-3-carbamoylpropanamido]-5-carbamimidamidopentanamido]-3-sulfanylpropanamido]-3-hydroxypropanamido]-4-carbamoylbutanamido]acetamido}-3-hydroxypropanamido]-3-sulfanylpropanamido]-3-(1H-indol-3-yl)propanamido]-3-carbamoylpropanoic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-{2-[(2S)-2-[(2S)-2-[(2R)-2-[(2S)-2-[(2S)-2-amino-3-carbamoylpropanamido]-5-carbamimidamidopentanamido]-3-sulfanylpropanamido]-3-hydroxypropanamido]-4-carbamoylbutanamido]acetamido}-3-hydroxypropanamido]-3-sulfanylpropanamido]-3-(1H-indol-3-yl)propanamido]-3-carbamoylpropanoic acid
• Synonyms: Asn-Arg-Cys-Ser-Gln-Gly-Ser-Cys-Trp-Asn, Reduced

Database IDs

• MDL Number: MFCD00798787
• PubChem SID: 162247935
• PubChem CID: 46181528

CALCULATED PROPERTIES

• Acid pKa: 3.3502746
• H Acceptors: 20
• H Donor: 22
• LogD (pH = 5.5): -14.353133
• LogD (pH = 7.4): -12.984042
• Log P: -12.88272
• Molar Refractivity: 287.6791 cm^3
• Polarizability: 109.31859 Å^3
• Polar Surface Area: 572.64 Å^2
• Rotatable Bonds: 36
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥85% (HPLC)
• Empirical Formula (Hill Notation): C44H67N17O16S2

DETAILS

Sigma Aldrich - A2602

Amino Acid Sequence
Asn-Arg-Cys-Ser-Gln-Gly-Ser-Cys-Trp-Asn
Biochem/physiol Actions
The activity of the enzymes protein disulfide-isomerase (PDI) and DsbA (a periplasmic protein thiol:disulfide oxidoreductase) can be monitored with this peptide. Oxidation of this dithiol peptide to the disulfide state is accompanied by a significant change in tryptophan fluorescence emission intensity. This permits the rapid determination of the pH-dependence of the activity of both enzymes.