Glysperin B

Glysperin B

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Category Antibiotics
Catalog number BBF-01272
CAS 78213-55-5
Molecular Weight 918.98
Molecular Formula C40H66N6O18
Purity ≥95%

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Description

It is produced by the strain of Bacillus cereus Nos. F173-B61 and F262-B54. It has anti-gram positive bacteria and negative bacteria (including aminoglycoside antibiotic resistant bacteria) activity, the antibacterial activity of main component Glysperin A is 2-4 times stronger than B and C.

Specification

Synonyms BU-2349 B; Antibiotic BU-2349 B
IUPAC Name 4-[(2S,3S,4R,5S)-4-[(2R,3R,4R,5R)-4-[(2S,3R,4R,5R,6S)-5-[(2R,3R,4S,5R,6R)-5-amino-3-[[(2R)-2-aminopropanoyl]amino]-4-hydroxy-6-methyloxan-2-yl]oxy-3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3,5-dihydroxy-6-methylideneoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-N-[3-(4-aminobutylamino)propyl]benzamide
Canonical SMILES CC1C(C(C(C(O1)OC2C(OC(C(C2O)O)OC3C(C(OC(=C)C3O)OC4C(OC(C4O)OC5=CC=C(C=C5)C(=O)NCCCNCCCCN)CO)O)CO)NC(=O)C(C)N)O)N
InChI InChI=1S/C40H66N6O18/c1-17(42)35(55)46-25-27(50)24(43)18(2)57-37(25)62-32-22(15-47)60-38(29(52)28(32)51)64-34-26(49)19(3)58-39(31(34)54)63-33-23(16-48)61-40(30(33)53)59-21-9-7-20(8-10-21)36(56)45-14-6-13-44-12-5-4-11-41/h7-10,17-18,22-34,37-40,44,47-54H,3-6,11-16,41-43H2,1-2H3,(H,45,56)(H,46,55)/t17-,18-,22+,23+,24+,25-,26+,27+,28-,29-,30+,31-,32+,33+,34-,37-,38+,39+,40-/m1/s1
InChI Key PGEKDAOSVRPCSY-AMGOUKICSA-N

Properties

Appearance Colorless Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 1197.2 °C at 760 mmHg
Melting Point 166 °C (dec.)
Density 1.47 g/cm3
Solubility Soluble in Water; Fairly soluble in Methanol, Ethanol

Reference Reading

1. Glysperin, a new antibiotic complex of bacterial origin. I. Production, isolation and properties
H Kawaguchi, M Konishi, T Tsuno, T Miyaki, K Tomita, K Matsumoto, K Fujisawa, H Tsukiura J Antibiot (Tokyo). 1981 Apr;34(4):381-9. doi: 10.7164/antibiotics.34.381.
Strains of Bacillus cereus produced a complex of new antibiotics, glysperins A, B and C. They are basic, water-soluble antibiotics and active against Gram-positive and Gram-negative bacteria including aminoglycoside-resistant organisms. Glysperin A is a major component of the antibiotic complex and approximately two to four times more active than components B and C.
2. Glysperin, a new antibiotic complex of bacterial origin. II. Structures of glysperins A, B and C
T Tsuno, M Konishi, T Naito, H Kawaguchi J Antibiot (Tokyo). 1981 Apr;34(4):390-402. doi: 10.7164/antibiotics.34.390.
Structures of glysperins A, B and C were determined on the basis of chemical degradation studies in conjunction with spectroscopic analyses. Glysperin A consisted of L-alanine, p-hydroxybenzoic acid, a C11-alkyl tetramine and four sugar moieties, three of which were identified as D-ribose, D-galactose and 2,4-diamino-2,4,6-trideoxy-D-galactose. The fourth sugar was a novel exoenose, 6-deoxy-D-xylo-hex-5-enose. Structural difference between glysperins A and B resided solely in the terminal polyamine moiety which was spermidine in glysperin B. Glysperin C contained D-glucose in place of the exoenohexose moiety of glysperin A. Glysperins A, B and C are, in some respects, structurally related to the glycocinnamoylspermidine antibiotics, LL-BM 123 beta, gamma 1 and gamma 2.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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