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Rp 71955

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Rp 71955 is an antibacterial peptide isolated from Streptomyces sp. It has activity against viruses.

Category

Functional Peptides

Catalog number

BAT-011172

Molecular Formula

C97H131N23O26S4

Molecular Weight

2163.5

Specification
Reference Reading

IUPAC Name

(2S)-2-[[(2S)-2-[[(1S,4S,7S,13R,19S,22S,25S,28S,31R,36R,39S,45S,51S,54R,60S)-60-(2-amino-2-oxoethyl)-4-benzyl-45-[(2S)-butan-2-yl]-39-(hydroxymethyl)-19-[(4-hydroxyphenyl)methyl]-7,22-dimethyl-51-(2-methylpropyl)-2,5,8,11,14,17,20,23,26,29,38,41,44,47,50,53,56,59,62-nonadecaoxo-25,28-di(propan-2-yl)-33,34,64,65-tetrathia-3,6,9,12,15,18,21,24,27,30,37,40,43,46,49,52,55,58,61-nonadecazatricyclo[34.21.5.413,54]hexahexacontane-31-carbonyl]amino]-3-phenylpropanoyl]amino]-3-(1H-indol-3-yl)propanoic acid

Synonyms

aborycin; Cys-Leu-Gly-Ile-Gly-Ser-Cys-Asn-Asp-Phe-Ala-Gly-Cys-Gly-Tyr-Ala-Val-Val-Cys-Phe-Trp

Sequence

(cyclo)-C(1)LGIGSC(2)ND-(cyclo)FAGC(1)GYAVVC(2)FW

InChI

InChI=1S/C97H131N23O26S4/c1-11-50(8)80-94(142)103-40-75(126)107-67(42-121)90(138)116-70-45-149-150-46-71(93(141)112-63(32-54-22-16-13-17-23-54)87(135)115-66(97(145)146)34-56-37-99-59-25-19-18-24-58(56)59)117-95(143)78(48(4)5)120-96(144)79(49(6)7)119-82(130)52(10)105-85(133)61(33-55-26-28-57(122)29-27-55)106-74(125)39-102-84(132)68-43-147-148-44-69(91(139)110-60(30-47(2)3)83(131)101-41-77(128)118-80)108-73(124)36-65(114-88(136)64(35-72(98)123)113-92(70)140)89(137)111-62(31-53-20-14-12-15-21-53)86(134)104-51(9)81(129)100-38-76(127)109-68/h12-29,37,47-52,60-71,78-80,99,121-122H,11,30-36,38-46H2,1-10H3,(H2,98,123)(H,100,129)(H,101,131)(H,102,132)(H,103,142)(H,104,134)(H,105,133)(H,106,125)(H,107,126)(H,108,124)(H,109,127)(H,110,139)(H,111,137)(H,112,141)(H,113,140)(H,114,136)(H,115,135)(H,116,138)(H,117,143)(H,118,128)(H,119,130)(H,120,144)(H,145,146)/t50-,51-,52-,60-,61-,62-,63-,64-,65-,66-,67-,68-,69-,70-,71-,78-,79-,80-/m0/s1

InChI Key

AJFZCVFYMNSDFP-NEKRQKPVSA-N

Canonical SMILES

CCC(C)C1C(=O)NCC(=O)NC(C(=O)NC2CSSCC(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)C(NC(=O)CNC(=O)C3CSSCC(C(=O)NC(C(=O)NCC(=O)N1)CC(C)C)NC(=O)CC(C(=O)NC(C(=O)NC(C(=O)NCC(=O)N3)C)CC4=CC=CC=C4)NC(=O)C(NC2=O)CC(=O)N)CC5=CC=C(C=C5)O)C)C(C)C)C(C)C)C(=O)NC(CC6=CC=CC=C6)C(=O)NC(CC7=CNC8=CC=CC=C87)C(=O)O)CO

1. Solution structure of RP 71955, a new 21 amino acid tricyclic peptide active against HIV-1 virus

D Fréchet, J D Guitton, F Herman, D Faucher, G Helynck, B Monegier du Sorbier, J P Ridoux, E James-Surcouf, M Vuilhorgne Biochemistry. 1994 Jan 11;33(1):42-50. doi: 10.1021/bi00167a006.

The structure of RP 71955, a new tricyclic 21 amino acid peptide active against human immunodeficiency virus 1, was determined. Its amino acid composition was inferred from the results of fast atom bombardment mass spectrometry, nuclear magnetic resonance, Raman spectroscopy, and amino acid analysis. Its sequence could not be determined classically, using Edman degradation, given the lack of a free terminal NH2. It was deduced from the interpretation of interresidue nuclear Overhauser effects and confirmed by the sequencing of peptides obtained by limited chemical hydrolysis. It was found to be CLGIGSCNDFAGCGYAVVCFW. An internal amide bond between the NH2 of C1 and the gamma-COOH of D9 was observed, as well as two disulfide bridges, one between C1 and C13 and one between C7 and C19. The three-dimensional structure of RP 71955 was determined from nuclear magnetic resonance derived constraints using distance geometry, restrained molecular dynamics, nuclear Overhauser effect back calculation, and an iterative refinement using a full relaxation matrix approach. Analogies between the structure of RP 71955 and some functional domains of gp41, the transmembrane protein of human immunodeficiency virus 1, suggest hypotheses concerning the mode of action of RP 71955.

3. Solution structure of endothelin B receptor selective antagonist RES-701-1 determined by 1H NMR spectroscopy

R Katahira, K Shibata, M Yamasaki, Y Matsuda, M Yoshida Bioorg Med Chem. 1995 Sep;3(9):1273-80. doi: 10.1016/0968-0896(95)00122-w.

The three-dimensional structure of the endothelin B receptor (ETB) selective antagonist RES-701-1 has been determined by 1H NMR in deuterated dimethyl sulphoxide. RES-701-1 consists of 16 amino acid residues with a novel internal linkage between the beta-carboxyl group of Asp9 and the alpha-amino group of Gly1. The structural calculations were carried out with the combined use of distance geometry and simulated annealing. The result indicates that RES-701-1 adopts an extraordinary folding; the 'tail' (Trp10-Trp16) passes through the 'ring' region (Gly1-Asp9). Several critical NOEs directly support this extraordinary folding. The folding of RES-701-1 turned out to be the same as that Frèchet et al. calculated for RP 71955 which possesses the same internal linkage as RES-701-1. The obtained structure suggested that the region consisting of Thr6, Ala7, Tyr14 and Tyr15 and/or, the region consisting of Asn2, Tyr14 and Tyr15 are involved in a binding with ETB.