diff --git a/src/javascript/functions.jsx b/src/javascript/functions.jsx
index 3581c5d..53b6a09 100644
--- a/src/javascript/functions.jsx
+++ b/src/javascript/functions.jsx
@@ -55,6 +55,32 @@ export function removeLeadingWhitespaces(string) {
     return string;
 }
 
+export function removeTrailingWhitespaces(string) {
+    while (string.charCodeAt(string.length - 1) === WHITESPACE_CHAR_CODE) {
+        string = string.substring(0, string.length - 1);
+    }
+    return string;
+}
+
+
+export function prefixAfterWhitespace(prefix, string) {
+    if (string.charCodeAt(0) == WHITESPACE_CHAR_CODE) {
+        string = removeLeadingWhitespaces(string);
+        return ' ' + prefix + string;
+    } else {
+        return prefix + string;
+    }
+}
+
+export function suffixBeforeWhitespace(string, suffix) {
+    if (string.charCodeAt(string.length - 1) == WHITESPACE_CHAR_CODE) {
+        string = removeTrailingWhitespaces(string);
+        return string + suffix + ' ';
+    } else {
+        return string + suffix;
+    }
+}
+
 export function isListItem(string) {
     return /^[\s]*[-•][\s].*$/g.test(string);
 }
diff --git a/src/javascript/models/StringFormat.jsx b/src/javascript/models/StringFormat.jsx
index 54a7041..3518c2f 100644
--- a/src/javascript/models/StringFormat.jsx
+++ b/src/javascript/models/StringFormat.jsx
@@ -9,17 +9,17 @@ StringFormat.initEnum({
     },
     BOLD: {
         needFormat: true,
-        startSymbol: '**',
-        endSymbol: '**'
+        startSymbol: ' **',
+        endSymbol: '** '
     },
     OBLIQUE: {
         needFormat: true,
-        startSymbol: '_',
-        endSymbol: '_'
+        startSymbol: ' _',
+        endSymbol: '_ '
     },
     BOLD_OBLIQUE: {
         needFormat: true,
-        startSymbol: '**_',
-        endSymbol: '_**'
+        startSymbol: ' **_',
+        endSymbol: '_** '
     }
 })
\ No newline at end of file
diff --git a/src/javascript/models/TextItemLineCompactor.jsx b/src/javascript/models/TextItemLineCompactor.jsx
index 62344f2..113149c 100644
--- a/src/javascript/models/TextItemLineCompactor.jsx
+++ b/src/javascript/models/TextItemLineCompactor.jsx
@@ -2,6 +2,7 @@ import TextItem from './TextItem.jsx';
 import { ParsedElements } from './PageItem.jsx';
 import { isNumber } from '../functions.jsx'
 import { sortByX } from '../textItemFunctions.jsx'
+import { prefixAfterWhitespace, suffixBeforeWhitespace } from '../functions.jsx';
 
 // Compact text items which have been grouped to a line (through TextItemLineCompactor) to a single TextItem doing inline transformations like 
 //'whitespace removal', bold/emphasis annotation, link-detection, etc..
@@ -71,19 +72,19 @@ export default class TextItemLineCompactor {
         const addStartSymbol = () => {
             resolvedLineItems.splice(openFormatIndex, 1, new TextItem({
                 ...openFormatItem,
-                text: openFormatType.startSymbol + openFormatItem.text
+                text: prefixAfterWhitespace(openFormatType.startSymbol, openFormatItem.text)
             }));
         }
         const addEndSymbol = (index) => {
             resolvedLineItems.splice(index, 1, new TextItem({
                 ...lastItem,
-                text: lastItem.text + openFormatType.endSymbol
+                text: suffixBeforeWhitespace(lastItem.text, openFormatType.endSymbol)
             }));
         }
         const addCompleteSymbol = () => {
             resolvedLineItems.splice(openFormatIndex, 1, new TextItem({
                 ...openFormatItem,
-                text: openFormatType.startSymbol + openFormatItem.text + openFormatType.endSymbol
+                text: suffixBeforeWhitespace(prefixAfterWhitespace(openFormatType.startSymbol, openFormatItem.text), openFormatType.endSymbol)
             }));
         }
 
diff --git a/test/functions.spec.js b/test/functions.spec.js
index 35ccbdc..221b04c 100644
--- a/test/functions.spec.js
+++ b/test/functions.spec.js
@@ -1,6 +1,6 @@
 import { expect } from 'chai';
 
-import { hasUpperCaseCharacterInMiddleOfWord, normalizedCharCodeArray, removeLeadingWhitespaces, charCodeArray, isListItem, isNumberedListItem, wordMatch } from '../src/javascript/functions.jsx'
+import { hasUpperCaseCharacterInMiddleOfWord, normalizedCharCodeArray, removeLeadingWhitespaces, removeTrailingWhitespaces, prefixAfterWhitespace, suffixBeforeWhitespace, charCodeArray, isListItem, isNumberedListItem, wordMatch } from '../src/javascript/functions.jsx'
 
 describe('hasUpperCaseCharacterInMiddleOfWord', () => {
 
@@ -54,6 +54,43 @@ describe('removeLeadingWhitespaces', () => {
 
 });
 
+describe('removeTrailingWhitespaces', () => {
+    it('No Removes', () => {
+        expect(removeTrailingWhitespaces(".")).to.be.equal(".");
+        expect(removeTrailingWhitespaces(" .")).to.be.equal(" .");
+        expect(removeTrailingWhitespaces(" . .")).to.be.equal(" . .");
+    });
+
+    it('Removes', () => {
+        expect(removeTrailingWhitespaces(". ")).to.be.equal(".");
+        expect(removeTrailingWhitespaces(".  ")).to.be.equal(".");
+        expect(removeTrailingWhitespaces(" . ")).to.be.equal(" .");
+        expect(removeTrailingWhitespaces(" . .  ")).to.be.equal(" . .");
+    });
+
+});
+
+
+describe('prefixAfterWhitespace', () => {
+    it('Basic', () => {
+        expect(prefixAfterWhitespace('1', '2')).to.be.equal('12');
+        expect(prefixAfterWhitespace(' 1', '2')).to.be.equal(' 12');
+        expect(prefixAfterWhitespace(' 1', ' 2')).to.be.equal('  12');
+        expect(prefixAfterWhitespace('1', ' 2')).to.be.equal(' 12');
+        expect(prefixAfterWhitespace('1', '  2')).to.be.equal(' 12');
+    });
+});
+
+describe('suffixBeforeWhitespace', () => {
+    it('Basic', () => {
+        expect(suffixBeforeWhitespace('A ', '.')).to.be.equal('A. ');
+        expect(suffixBeforeWhitespace(' A', '.')).to.be.equal(' A.');
+        expect(suffixBeforeWhitespace(' A ', ' .')).to.be.equal(' A . ');
+        expect(suffixBeforeWhitespace('A', ' .')).to.be.equal('A .');
+        expect(suffixBeforeWhitespace('A  ', '.')).to.be.equal('A. ');
+    });
+});
+
 
 describe('charCodeArray', () => {
     it('Charcodes', () => {